Information on EC 3.1.1.53 - sialate O-acetylesterase

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The expected taxonomic range for this enzyme is: Ruminococcus

EC NUMBER
COMMENTARY
3.1.1.53
-
RECOMMENDED NAME
GeneOntology No.
sialate O-acetylesterase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
N-acetyl-O-acetylneuraminate + H2O = N-acetylneuraminate + acetate
show the reaction diagram
acts on free and glycosidically bound N-acetyl- or N-glycoloyl-neuraminic acid, acts mainly on the 4-O- and 9-O-acetyl groups. Also acts on some other O-acetyl esters, both cyclic and acyclic compounds, which are not sialic acids
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
acetylation
-
of monomeric sialic acids
acetylation
-
of monomeric sialic acids
-
hydrolysis of carboxylic ester
-
-
-
-
SYSTEMATIC NAME
IUBMB Comments
N-acyl-O-acetylneuraminate O-acetylhydrolase
Acts on free and glycosidically bound N-acetyl- or N-glycoloyl-neuraminic acid; acts mainly on the 4-O- and 9-O-acetyl groups. Also acts on some other O-acetyl esters, both cyclic and acyclic compounds, which are not sialic acids.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
9(4)-O-acetylesterase
-
-
9(4)-O-acetylesterase
influenza C virus Johannesburg/1/66
-
-
-
9-O-acetyl N-acetylneuraminic acid esterase
-
-
9-O-acetyl sialic acid esterase
-
Siae gene encodes two splice forms
9-O-acetylsialic acid esterase
-
-
9-O-acetylsialic acid esterase
influenza C virus Johannesburg/1/66
-
-
-
BCoVHE
P15776
-
cytosolic sialate:O-acetylesterase
-
-
cytosolic sialic acid 9-O-acetylesterase
-
-
haemagglutinin esterase
-
-
haemagglutinin esterase
bovine coronavirus BcoV
-
-
-
haemagglutinin esterase fusion
P07975
-
haemagglutinin esterase fusion
influenza C virus INF-C
P07975
-
-
HE
bovine coronavirus BcoV
-
-
-
HEF
P07975
-
HEF
influenza C virus INF-C
P07975
-
-
hemagglutinin esterase
-
-
hemagglutinin-esterase
-
-
hemagglutinin-esterase
P15776
-
hemagglutinin-esterase
-
-
hemagglutinin-esterase
-
-
hemagglutinin-esterase
Murine coronavirus DVIM
-
-
-
INF-C esterase
P07975
-
INF-C esterase
influenza C virus INF-C
P07975
-
-
intralumenal sialate: 9-O-acetylesterase
-
-
Lse
-
one splice variant
lysosomal sialic acid 9-O-acetylesterase
-
-
O-acetylsialic acid esterase
-
-
recHE4
-
recombinant HE
SIAE
-
-
sialate 9-O-acetylesterase
-
-
sialate 9-O-acetylesterase
-
-
sialate esterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
Murine coronavirus DVIM
-
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterase
-
-
sialate-O-acetylesterases
-
-
sialate-O-acetylesterases
-
-
sialate: O-acetyl esterase
-
-
sialic acid acetyl esterase
-
-
sialic acid O-acetylesterase
-
-
sialic acid O-acetylesterase
-
-
sialic acid O-acetylesterase
-
-
Sialic acid-specific 9-O-acetylesterase
-
-
-
-
sialyl O-acetyl esterase
-
-
sialyl O-acetyl esterase
-
-
-
SOAE
-
-
lysosomal sialic acid O-acetylesterase
-
-
additional information
-
NanS belongs to the SGNH superfamily of hydrolases
CAS REGISTRY NUMBER
COMMENTARY
89400-31-7
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
starfish
-
-
Manually annotated by BRENDA team
VIII-271C, VIII-271G, VIII-271E, VIII-271F, isolated from human faeces
-
-
Manually annotated by BRENDA team
VIII-210, isolated from human faeces
-
-
Manually annotated by BRENDA team
X-95, isolated from human faeces
-
-
Manually annotated by BRENDA team
VII-240, isolated from human faeces
-
-
Manually annotated by BRENDA team
BcoV, strain Mebus
UniProt
Manually annotated by BRENDA team
bovine coronavirus BcoV
BcoV
-
-
Manually annotated by BRENDA team
X-18B, isolated from human faeces
-
-
Manually annotated by BRENDA team
17A, 17B, 17C, 17D, V-64C, O86, isolated from human faeces
-
-
Manually annotated by BRENDA team
gene nanS, part of the nanCMS operon
-
-
Manually annotated by BRENDA team
ISAV 4, isolate 4, Glesvaer/2/90
-
-
Manually annotated by BRENDA team
strain Johannesburg/1/66
-
-
Manually annotated by BRENDA team
influenza C virus INF-C
INF-C
UniProt
Manually annotated by BRENDA team
influenza C virus Johannesburg/1/66
strain Johannesburg/1/66
-
-
Manually annotated by BRENDA team
MHV-DVIM, a Murine coronavirus, MuCoV, or Mouse hepatitis virus, MHV, species
-
-
Manually annotated by BRENDA team
Murine coronavirus DVIM
MHV-DVIM, a Murine coronavirus, MuCoV, or Mouse hepatitis virus, MHV, species
-
-
Manually annotated by BRENDA team
MHV-A59,a Murine coronavirus, MuCoV, or Mouse hepatitis virus, MHV, species
-
-
Manually annotated by BRENDA team
MHV-S, a Murine coronavirus, MuCoV, or Mouse hepatitis virus, MHV, species
-
-
Manually annotated by BRENDA team
; C57BL/6 wild-type or homozygous Siae deficient knockout mice, and B6.129S7-Rag1-deficient mice
-
-
Manually annotated by BRENDA team
no activity in Dictyostelium discoideum
-
-
-
Manually annotated by BRENDA team
no activity in Glycine max
-
-
-
Manually annotated by BRENDA team
no activity in Hirudo medicinalis
medicinal leech
-
-
Manually annotated by BRENDA team
no activity in Nicotiana tabacum
-
-
-
Manually annotated by BRENDA team
no activity in Spodoptera frugiperda
fall armyworm, Sf-9 cells
-
-
Manually annotated by BRENDA team
male Sprague-Dawley
-
-
Manually annotated by BRENDA team
VI-268, isolated from human faeces
-
-
Manually annotated by BRENDA team
IX-70, VIII-239, isolated from human faeces
-
-
Manually annotated by BRENDA team
serotype 2
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
evolution
-
in apparent contrast to human and ungulate host range variants of Betacoronavirus-1, murine coronaviruses actually bind to O-Ac-sialic acids via hemagglutinin-esterase exclusively. Apparently, expansion of group A betacoronaviruses into new hosts and niches is accompanied by changes in hemagglutinin-esterase ligand and substrate preference and in the roles of hemagglutinin-esterase and sialidase in Sia receptor usage
evolution
-
although the backbone of the structure is similar to previously characterized family members, sequence comparisons indicate that this family can be further subdivided into two subfamilies with somewhat different fingerprints. NanS is the founding member of group II. Sequence motifs and two subfamilies of SGNH hydrolases, overview
evolution
Murine coronavirus DVIM
-
in apparent contrast to human and ungulate host range variants of Betacoronavirus-1, murine coronaviruses actually bind to O-Ac-sialic acids via hemagglutinin-esterase exclusively. Apparently, expansion of group A betacoronaviruses into new hosts and niches is accompanied by changes in hemagglutinin-esterase ligand and substrate preference and in the roles of hemagglutinin-esterase and sialidase in Sia receptor usage
-
malfunction
-
mice with a mutation in sialate: O-acetyl esterase (inframe deletion of exon 2, resulting in a protein lacking esterase activity) exhibit enhanced B cell receptor activation, defects in peripheral B cell development, and spontaneously develop antichromatin autoantibodies and glomerular immune complex deposits. The 9-O-acetylation state of sialic acid regulates the function of CD22, a Siglec that functions in vivo as an inhibitor of BCR signaling
physiological function
-
the O-acetylesterase is probably essential for the synthesis of capsular Neu5Ac in Streptococcus suis
physiological function
-
besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Bovine coronavirus exhibits sialate-9-O-acetylesterase specificity
physiological function
-
besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Influenza C virus exhibits sialate-9-O-acetylesterase specificity
physiological function
-
besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Mouse hepatitis virus strain S exhibits sialate-4-O-acetylesterase specificity
physiological function
-
besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Rat sialoadacryoadenitis coronavirus exhibits sialate-4-O-acetylesterase specificity
physiological function
-
sialate-O-acetylesterases, SIAE, are important enzymes in sialic acid metabolism. They hydrolyse 4- or 9-O-acetyl groups of either glycosidically linked or free sialic acids released from glycoconjugates by sialidases. Both sialate-O-acetylesterase, SIAE, and sialate-O-acetyltranferase, SOAT, activities seem to be responsible for the enhanced level of Neu5,9Ac2 in lymphoblasts, which is a hall mark in acute lymphoblastic leukemia
malfunction
-
decreased sialate-O-acetylesterase activity occurs both in lysosomal and cytosolic fractions of childhood acute lymphoblastic leukemia, ALL, cell lines and primary cells from bone marrow of patients compared to peripheral blood mononuclear cells from healthy donors, which preferentially hydrolyse O-acetyl groups at C-9 of Sia
additional information
-
SsNeuAc contains a asignature consensus sequence for serine esterase, Gly-Xaa-Ser-Xaa-Gly, is found within the C-terminal half
additional information
-
the NanS catalytic center contains Ser19 and His301 but no Asp/Glu is present to form the classical catalytic triad
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-deoxy-2,3-didehydro-N-acetyl-9-O-acetylneuraminate + H2O
?
show the reaction diagram
-
55% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
2-deoxy-2,3-didehydro-N-acetyl-9-O-acetylneuraminate + H2O
?
show the reaction diagram
-
37% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
3'-O-acetylthymidine + H2O
thymidine + acetate
show the reaction diagram
-
8% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
show the reaction diagram
-
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
show the reaction diagram
-
-
-
-
-
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
show the reaction diagram
-
130% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
show the reaction diagram
-
220% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
4-methylumbelliferyl acetate + H2O
4-methylumbelliferone + acetate
show the reaction diagram
influenza C virus Johannesburg/1/66
-
-
-
-
-
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferone + butyrate
show the reaction diagram
-
less than 5% of the activity compared to 4-methylumbelliferyl acetate at pH 5.5
-
-
-
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferone + butyrate
show the reaction diagram
-
14% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
3500% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
72% of the activity compared to 4-methylumbelliferyl acetate at pH 5.5
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
680% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
influenza C virus Johannesburg/1/66
-
3500% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
4-nitrophenyl acetate + H2O
4-nitrophenol + acetate
show the reaction diagram
Murine coronavirus DVIM
-
-
-
-
?
4-nitrophenylacetate + H2O
4-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
4-O-acetyl sialic acid + H2O
sialic acid + acetate
show the reaction diagram
-
-
-
-
?
5-N-acetyl-4,9-di-O-acetylneuraminic acid alpha-methylglycoside + H2O
4,9-di-O-acetylneuraminic acid alpha-methylglycoside + acetate
show the reaction diagram
P15776
sialate-9-O-acetylesterase activity
analysis by gas chromatography/mass spectrometry
-
?
5-N-acetyl-7(8),9-di-O-acetylneuraminic acid + H2O
?
show the reaction diagram
-
-
-
?
5-N-acetyl-9-O-acetylneuraminic acid + H2O
5-N-acetylneuraminic acid + acetate
show the reaction diagram
-
-
-
?
9-O-acetyl sialic acid + H2O
sialic acid + acetate
show the reaction diagram
-
-
-
-
?
9-O-acetyl sialic acid + H2O
sialic acid + acetate
show the reaction diagram
-
-
-
-
?
9-O-acetyl-N-acetylneuraminic acid + H2O
N-acetylneuraminic acid + acetate
show the reaction diagram
-
-
-
-
?
acetyl-CoA + H2O
CoA + acetate
show the reaction diagram
-
-
-
?
acetyl-CoA + H2O
CoA + acetate
show the reaction diagram
-
2% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
alacepril + H2O
deacetylalacepril + acetate
show the reaction diagram
-
-
-
?
alpha-naphthyl acetate + H2O
alpha-naphthol + acetate
show the reaction diagram
-
-
-
?
alpha-naphthyl acetate + H2O
1-naphthol + acetate
show the reaction diagram
-
-
-
-
-
alpha-naphthyl acetate + H2O
1-naphthol + acetate
show the reaction diagram
-
2200% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
alpha-naphthyl acetate + H2O
1-naphthol + acetate
show the reaction diagram
-
65% of the activity compared to 4-methylumbelliferyl acetate at pH 5.5
-
-
-
alpha-naphthyl acetate + H2O
1-naphthol + acetate
show the reaction diagram
-
643% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
bovine submandibular gland mucin + H2O
?
show the reaction diagram
-
no hydrolysis
-
-
-
bovine submandibular gland mucin + H2O
?
show the reaction diagram
-
30% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
bovine submaxillary mucin + H2O
?
show the reaction diagram
-
-
-
-
?
CMP-O-acetylneuraminadate + H2O
?
show the reaction diagram
-
SsNeuA is a bifunctional CMP-Neu5Ac synthetase/O-acetylesterase, which strictly de-O-acetylates CMP-O-acetyl-Neu5Ac
-
-
?
cytidine 5'-monophospho-N-acetylneuraminic acid + H2O
?
show the reaction diagram
-
-
-
-
?
methyl 6-O-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + H2O
methyl 6-O-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate
show the reaction diagram
-
methyl N-acetylneuraminide, 25C, 60 min, pH 7
NMR-based enzyme assay
-
?
methyl 6-S-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-6-thio-alpha-D-glucoside + H2O
methyl 6-S-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate
show the reaction diagram
-
thio-linked N-acetylneuraminosylglucoside, 25C, 60 min, pH 7
NMR-based enzyme assay
-
?
methyl 6-S-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-6-thio-alpha-D-glucoside + H2O
methyl 6-S-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate
show the reaction diagram
P07975
thio-linked N-acetylneuraminosylglucoside, 25C, 60 min, pH 7
NMR-based enzyme assay
-
?
N-acetyl-4-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
60% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-4-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
3% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-4-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
no hydrolysis at pI 4.8, same rate of hydrolysis at pI 5.7 compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-4-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
influenza C virus Johannesburg/1/66
-
3% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-4-O-acetylneuraminic acid + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
pH 8, 30 min, 37C, catalysed only by esterase with pI 5.7
analyses by HPLC
-
?
N-acetyl-9-O-acetyl-neuraminic acid + H2O
N-acetylneuraminic acid + acetate
show the reaction diagram
-
25C, 60 min, pH 7, slow activity due to alpha: beta anomeric ratio of about 5: 95
NMR-based enzyme assay
-
?
N-acetyl-9-O-acetyl-neuraminic acid + H2O
N-acetylneuraminic acid + acetate
show the reaction diagram
P07975
25C, 60 min, pH 7, slow activity due to alpha: beta anomeric ratio of about 5:95
NMR-based enzyme assay
-
?
N-acetyl-9-O-acetyl-neuraminic acid alpha-methylglycoside + H2O
N-acetylneuraminic acid alpha-methylglycoside + acetate
show the reaction diagram
P07975
methyl N-acetylneuraminide, 25C, 60 min, pH 7
NMR-based enzyme assay
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
P70665
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
at pI 4.8 and pI 5.7
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
influenza C virus Johannesburg/1/66
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
-
-
-
?
N-acetyl-9-O-acetylneuraminate beta-methylglycoside + H2O
N-acetylneuraminate beta-methylglycoside + acetate
show the reaction diagram
-
70% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-9-O-acetylneuraminate lactose + H2O
N-acetylneuraminate lactose + acetate
show the reaction diagram
-
96% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-9-O-acetylneuraminate lactose + H2O
N-acetylneuraminate lactose + acetate
show the reaction diagram
-
same rate of hydrolysis compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-9-O-acetylneuraminate lactose + H2O
N-acetylneuraminate lactose + acetate
show the reaction diagram
influenza C virus Johannesburg/1/66
-
96% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
N-acetyl-9-O-acetylneuraminic acid + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
pH 8, 30 min, 37C, catalysed by esterase with pI 4.8 and esterase with pI 5.7
analyses by HPLC
-
?
N-acetyl-9-O-acetylneuraminic acid + H2O
?
show the reaction diagram
-
-
-
-
?
N-acetyl-O-9-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
best substrate, contribution of Ser19 and His301 to catalysis, active site structure, overview
-
-
?
N-acetyl-O-acetylneuraminate + H2O
?
show the reaction diagram
-
-
-
-
-
N-acetyl-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
destroys receptors on the surface of the target cells
-
-
?
O-9-acetyl-GD3-S-phenyl + H2O
?
show the reaction diagram
-
i.e. 9-O-acetyl-NeuAcalpha-2,8-NeuAcalpha-2,3-Galbeta-1,4-Glcbeta-S-phenyl
-
-
?
O-acetylserine + H2O
serine + acetate
show the reaction diagram
-
less than 5% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
show the reaction diagram
-
-
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
show the reaction diagram
P07975
-
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
show the reaction diagram
P15776
-
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
show the reaction diagram
-
pH 8
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
show the reaction diagram
bovine coronavirus BcoV
-
-
-
-
?
p-nitrophenyl acetate + H2O
p-nitrophenol + acetate
show the reaction diagram
influenza C virus INF-C
P07975
-
-
-
?
rat serum glycoprotein + H2O
?
show the reaction diagram
-
90% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
spironolactone + H2O
?
show the reaction diagram
-
-
-
?
thiophenyl acetate + H2O
thiophenol + acetate
show the reaction diagram
-
12% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
thiophenyl acetate + H2O
thiophenol + acetate
show the reaction diagram
-
305% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
triacetin + H2O
?
show the reaction diagram
-
26% of the activity compared to N-acetyl-9-O-acetylneuraminate
-
-
?
methyl 6-S-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-6-thio-alpha-D-glucoside + H2O
methyl 6-S-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate
show the reaction diagram
bovine coronavirus BcoV
-
thio-linked N-acetylneuraminosylglucoside, 25C, 60 min, pH 7
NMR-based enzyme assay
-
?
additional information
?
-
-
no hydrolysis with N-acetyl-4-O-lactoylneuraminate, N-acetyl-9-O-acetylneuraminate methyl ester
-
-
-
additional information
?
-
-
no hydrolysis with acetyl-coenzyme A, acetylthiocholine iodide
-
-
-
additional information
?
-
-
no hydrolysis with N-glycoloyl-9-O-lactoylneuraminate, bovine submandibular gland mucin, rat serum glycoprotein, rat erythrocytes
-
-
-
additional information
?
-
-
strict substrate specificity for O-acetylated acids and a broad specificity for small synthetic esters, little or no activity against natural acetylated compounds other than sialic acids
-
-
-
additional information
?
-
-
LSE can act only on O-acetyl-esters at the 9-position of sialic acids
-
-
-
additional information
?
-
-
no hydrolysis with N-acetyl-7-O-acetylneuraminate, horse alpha1-acid glycoprotein, N-acetylneuraminate methyl ester
-
-
-
additional information
?
-
-
specifically hydrolyses 9-O-acetylgroups on sialic acid
-
?
additional information
?
-
-
O-acetyl esters
-
-
-
additional information
?
-
-
O-acetyl esters, specific for sialic acids and selectively cleaves acetyl groups at the 9-position. it deacetylates di-O-acetyl- and tri-O-acetyl-N-acetylneuraminic acids by first cleaving the O-acetyl ester at the 9-position. The 7- and 8-acetylesters then undergo spontaneous migration to the 9-position, where they can be cleaved
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
incubation of the enzyme with chicken erythrocytes abolishes the agglutinability the erythrocytes
-
-
-
additional information
?
-
-
alpha-anomer specificity
-
-
-
additional information
?
-
P07975
alpha-anomer specificity
-
-
-
additional information
?
-
-
enhanced B-cell receptor signalling through hyper-9-O-acetylation of alpha2-6-linked sialic acid on N-glycans and defective CD22 inhibitory signalling in absence of the enzyme
-
-
-
additional information
?
-
P15776
purified enzyme destroys BCoV receptors on rat erythrocytes and Madin-Darby bovine kidney (MDBK) cells
-
-
-
additional information
?
-
P07975
Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling
-
-
-
additional information
?
-
-
alpha-naphthylacetate, 9-O-acetyl sialyllactose, serum alpha1 acid glycoprotein, and erythrocyte membranes containing N-acetyl-4-O-acetylneuraminic acid or N-acetyl-9-O-acetylneuraminic acid are susceptible to SOAE catalysed hydrolysis
-
-
-
additional information
?
-
P07975
enzyme activity independent of chemical nature of aglycon moiety
-
-
-
additional information
?
-
-
glycosidically linked sialic acids are also substrate, hydrolysis of 20% under standard conditions, liberation of sialic acid from gland mucin (mainly containing N-acetyl-4-O-acetylneuraminic acid), N-acetyl-4-O-acetylneuraminic acid is slightly preferred over N-acetyl-9-O-acetylneuraminic acid as substrate for esterase with pI 5.7, N-acetyl-7-O-acetylneuraminic acid is no substrate
-
-
-
additional information
?
-
-
specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25C, pH 7)
-
-
-
additional information
?
-
P07975
specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25C, pH 7)
-
-
-
additional information
?
-
-
substrate specificity towards aglycon moiety
-
-
-
additional information
?
-
-
MHV Sia receptor-binding specificity corresponds to the sialate-O-acetylesterase substrate preference of hemagglutinin-esterase , and hemagglutinin-esterase is sufficient to mediate virion binding to natural sialoglycoconjugates
-
-
-
additional information
?
-
-
MHV Sia receptor-binding specificity corresponds to the sialate-O-acetylesterase substrate preference of hemagglutinin-esterase, and hemagglutinin-esterase is sufficient to mediate virion binding to natural sialoglycoconjugates
-
-
-
additional information
?
-
-
the enzyme of Bovine coronavirus exhibits sialate-9-O-acetylesterase specificity
-
-
-
additional information
?
-
-
the enzyme of Influenza C virus exhibits sialate-9-O-acetylesterase specificity
-
-
-
additional information
?
-
-
the enzyme of Influenzy C virus exhibits sialate-4-O-acetylesterase specificity
-
-
-
additional information
?
-
-
the enzyme of Rat sialoadacryoadenitis coronavirus exhibits sialate-4-O-acetylesterase specificity
-
-
-
additional information
?
-
-
NanS is also active on phenylacetate, butylacetate, triacetin, and slightly on rosmarinic acid and propylacetate, substrate specificity, overview. NanS shows negligible aryl esterase activity with alpha-naphthyl acetate and alpha-naphthyl propionate as substrates and no measurable lipolytic activity or thioesterase activity
-
-
-
additional information
?
-
bovine coronavirus BcoV
-
alpha-anomer specificity, specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25C, pH 7), substrate specificity towards aglycon moiety
-
-
-
additional information
?
-
influenza C virus INF-C
P07975
alpha-anomer specificity, Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling, enzyme activity independent of chemical nature of aglycon moiety, specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25C, pH 7)
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
Murine coronavirus DVIM
-
MHV Sia receptor-binding specificity corresponds to the sialate-O-acetylesterase substrate preference of hemagglutinin-esterase , and hemagglutinin-esterase is sufficient to mediate virion binding to natural sialoglycoconjugates
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
N-acetyl-O-9-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
contribution of Ser19 and His301 to catalysis, active site structure, overview
-
-
?
N-acetyl-O-acetylneuraminate + H2O
?
show the reaction diagram
-
-
-
-
-
N-acetyl-O-acetylneuraminate + H2O
N-acetylneuraminate + acetate
show the reaction diagram
-
destroys receptors on the surface of the target cells
-
-
?
CMP-O-acetylneuraminadate + H2O
?
show the reaction diagram
-
SsNeuA is a bifunctional CMP-Neu5Ac synthetase/O-acetylesterase, which strictly de-O-acetylates CMP-O-acetyl-Neu5Ac
-
-
?
additional information
?
-
-
O-acetyl esters
-
-
-
additional information
?
-
-
O-acetyl esters, specific for sialic acids and selectively cleaves acetyl groups at the 9-position. it deacetylates di-O-acetyl- and tri-O-acetyl-N-acetylneuraminic acids by first cleaving the O-acetyl ester at the 9-position. The 7- and 8-acetylesters then undergo spontaneous migration to the 9-position, where they can be cleaved
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
-
alpha-anomer specificity
-
-
-
additional information
?
-
P07975
alpha-anomer specificity
-
-
-
additional information
?
-
-
enhanced B-cell receptor signalling through hyper-9-O-acetylation of alpha2-6-linked sialic acid on N-glycans and defective CD22 inhibitory signalling in absence of the enzyme
-
-
-
additional information
?
-
P15776
purified enzyme destroys BCoV receptors on rat erythrocytes and Madin-Darby bovine kidney (MDBK) cells
-
-
-
additional information
?
-
P07975
Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling
-
-
-
additional information
?
-
-
MHV Sia receptor-binding specificity corresponds to the sialate-O-acetylesterase substrate preference of hemagglutinin-esterase , and hemagglutinin-esterase is sufficient to mediate virion binding to natural sialoglycoconjugates
-
-
-
additional information
?
-
-
MHV Sia receptor-binding specificity corresponds to the sialate-O-acetylesterase substrate preference of hemagglutinin-esterase, and hemagglutinin-esterase is sufficient to mediate virion binding to natural sialoglycoconjugates
-
-
-
additional information
?
-
-
the enzyme of Bovine coronavirus exhibits sialate-9-O-acetylesterase specificity
-
-
-
additional information
?
-
-
the enzyme of Influenza C virus exhibits sialate-9-O-acetylesterase specificity
-
-
-
additional information
?
-
-
the enzyme of Influenzy C virus exhibits sialate-4-O-acetylesterase specificity
-
-
-
additional information
?
-
-
the enzyme of Rat sialoadacryoadenitis coronavirus exhibits sialate-4-O-acetylesterase specificity
-
-
-
additional information
?
-
bovine coronavirus BcoV
-
alpha-anomer specificity
-
-
-
additional information
?
-
influenza C virus INF-C
P07975
alpha-anomer specificity, Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
additional information
?
-
Murine coronavirus DVIM
-
MHV Sia receptor-binding specificity corresponds to the sialate-O-acetylesterase substrate preference of hemagglutinin-esterase , and hemagglutinin-esterase is sufficient to mediate virion binding to natural sialoglycoconjugates
-
-
-
additional information
?
-
-
O-acetylated sialic acids
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Cu2+
-
1 mM, block of essential SH-groups
Hg2+
-
1 mM, block of essential SH-groups
NaCl
-
150 mM, inhibitory at 500 mM when pH below pH 8
Zn2+
-
1 mM, block of essential SH-groups
Mg2+
-
activates
additional information
-
no divalent cation requirement
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2,3-Butanedione
-
irreversibly inactivated
2,3-Butanedione
-
inhibited by this arginine-modifying reagents, an essential arginine residue in the active site is important for substrate recognition
2-alpha-thiomethylmercuryl 9-acetamido-9-deoxy sialoside
-
competitive inhibition, Ki: 4.2 mM; the inhibitor is used to prepare heavy atom derivatives of the crystals
9-acetamido-N-acetyl-O-acetylneuraminate
-
no effect up to 5 mM
-
9-acetamido-N-acetyl-O-acetylneuraminate
-
little effect at 5 mM
-
Alpha-naphthyl acetate
-
competitive inhibitor
ammonium (allyl 5-acetamido-3,5-dideoxy-4-O-methyl-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
-
-
ammonium (allyl 5-acetamido-9-O-methyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
-
-
bis-p-nitrophenyl phosphate
-
little effect on the activity
CHAPS
-
lowers the activity by 40%
Cu2+
-
complete inhibition at 1 mM
deoxycholate
-
75-80% loss of activity at 2% concentration
diammonium (allyl 5-acetamido-3,5-dideoxy-4-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
-
-
diammonium (allyl 5-acetamido-3,5-dideoxy-9-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
-
-
Diethyl-4-nitrophenylphosphate
-
50% inhibition at 0.0024 mM
Diethyl-4-nitrophenylphosphate
-
-
Diethyl-4-nitrophenylphosphate
-
50% inhibition at 0.24 mM
Diethyl-4-nitrophenylphosphate
-
-
Diethyl-4-nitrophenylphosphate
-
irreversibly inactivated
diisopropyl fluorophosphate
-
DFP strong inhibition
diisopropyl fluorophosphate
-
50% inhibition at 0.35 mM
diisopropyl fluorophosphate
-
-
diisopropyl fluorophosphate
-
50% inhibition at 0.01 mM
diisopropyl fluorophosphate
-
-
diisopropyl fluorophosphate
-
-
diisopropyl fluorophosphate
-
irreversibly inactivated
diisopropyl fluorophosphates
-
complete inhibition at 1 mM
diisopropylfluorophosphate
-
1 mM, 25C, 15 min, total loss of activity
F-
-
little effect on the activity
Hg2+
-
complete inhibition at 1 mM
Hg2+
-
50% inhibition at 0.0035 mM
N-acetyl-9-O-acetylneuraminate
-
substrate inhibition above 2 mM
p-chloromercuribenzoate
-
little effect on the activity
Paraoxon
-
diethyl-4-nitrohenylphosphate (E600), 1 mM at 25C within 15 min leads to total loss of activity
Phenylglyoxal
-
irreversibly inactivated
Phenylglyoxal
-
inhibited by this arginine-modifying reagents, an essential arginine residue in the active site is important for substrate recognition
phenylmethylsulfonyl fluoride
-
complete inhibition at 10 mM
physostigmine
-
25% inhibition at 10 mM
physostigmine
-
25% inhibition at 10 mM
PMSF
-
45% inhibition at 1 mM
Hg2+
-
little effect on the activity
additional information
-
no inhibition by PMSF
-
additional information
-
bis-(4-nitrophenyl)phosphate, 1 mM Ca2+, 1 mM ethylene diaminotetraacetate (EDTA) without influence on activity
-
additional information
-
synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-O-acetylesterase from Influenza C virus. No inhibition of Bovine coronavirus by ammonium (allyl 5-acetamido-3,5-dideoxy-4-O-methyl-D-glycero-alpha-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-4-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
additional information
-
synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-Oacetylesterase from Influenza C virus. No inhibition of Influenza C virus by ammonium (allyl 5-acetamido-3,5-dideoxy-4-O-methyl-D-glycero-a-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-4-O-(P-methylphosphonyl)-D-glycero-a-d-galacto-2-nonulopyranosidonate)
-
additional information
-
synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-O-acetylesterase from Influenza C virus. No inhibition of Mouse hepatitis virus strain S by ammonium (allyl 5-acetamido-9-O-methyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-9-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
additional information
-
synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-O-acetylesterase from Influenza C virus. No inhibition of Rat sialoadacryoadenitis coronavirus by ammonium (allyl 5-acetamido-9-O-methyl-3,5-dideoxy-dglycero-alpha-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-9-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
additional information
-
not affected by detergents, i.e. Triton X-100, Triton CF-54, saponin; not affected by EDTA
-
additional information
-
not affected by detergents, i.e. Triton X-100, Triton CF-54, saponin
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.13
-
4-Methylumbelliferyl acetate
-
-
0.17
-
4-Methylumbelliferyl acetate
-
-
0.3
-
4-O-acetyl-sialic acid
-
low pI esterase form, obtained with free sialic acid
1.1
-
9-O-acetyl-sialic acid
-
low pI esterase form, obtained with free sialic acid
1.3
-
9-O-acetyl-sialic acid
-
high pI esterase form, obtained with free sialic acid
1.28
-
acetyl-CoA
-
pH 7.5, 37C
22
-
alacepril
-
pH 7.5, 37C
1.71
-
Alpha-naphthyl acetate
-
pH 7.5, 37C
0.8
-
N-acetyl-9-O-acetylneuraminic acid
-
-
1.1
-
N-acetyl-9-O-acetylneuraminic acid
-
-
8.8
-
N-acetyl-9-O-acetylneuraminic acid
-
-
18
-
N-acetyl-9-O-acetylneuraminic acid
-
-
0.9
-
N-acetyl-9-O-acetylneuraminic acid lactose
-
-
-
24
-
N-acetyl-9-O-acetylneuraminic acid lactose
-
-
-
0.652
-
spironolactone
-
pH 7.5, 37C
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
additional information
-
additional information
-
methyl-linked N-acetyl-neuraminide (N-acetyl-9-O-acetyl-neuraminic acid alpha-methylglycoside) hydrolysed at higher rate than thio-linked N-acetylneuraminosylglucoside (N-acetyl-9-O-acetyl-2,6-alpha-S-glucosyl-neuraminic acid alpha-methylglycoside)
-
additional information
-
additional information
P07975
methyl-linked N-acetyl-neuraminide (N-acetyl-9-O-acetyl-neuraminic acid alpha-methylglycoside) and thio-linked N-acetylneuraminosylglucoside (N-acetyl-9-O-acetyl-2,6-alpha-S-glucosyl-neuraminic acid alpha-methylglycoside) hydrolysed at similar rates
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Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
4.2
-
2-alpha-thiomethylmercuryl 9-acetamido-9-deoxy sialoside
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-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.00012
-
-
homogenate
0.05
-
-
specific activity in the commercial enzyme product Novarom G
0.104
-
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after preparative isoelectric focussing, pI 4.8
0.12
-
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specific activity in the commercial enzyme product Ultrazym
0.15
-
-
-
0.17
-
-
strain VI-268
0.19
-
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strain VIII-239
0.31
-
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strain IX-70
0.4
-
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specific activity in the commercial enzyme product Vinozym
0.465
-
-
-
0.71
-
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specific activity in the commercial enzyme product AR2000
0.84
-
-
4-methylumbelliferyl acetate as substrate
1.29
-
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substrate O-9-acetyl-GD3-S-phenyl, pH 7.2, 25C
1.8
-
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purified recombinant 29 kDa O-acetylesterase fragment, pH 7.2, 37C
2.31
-
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substrate N-acetyl-O-9-acetylneuraminate, pH 7.2, 25C
11.6
-
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alpha-naphthyl acetate as substrate
12.8
-
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4-nitrophenyl acetate as substrate
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.2
-
-
assay at
7.4
-
-
-
7.5
-
-
assay at
7.8
-
-
-
8
8.5
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substrate 4-nitrophenyl acetate, wild-type SsNeuA and mutant SsNeuA234-410
8
-
-
HEPES buffer, activity affected at high NaCl concentrations (500 mM)
8.4
8.6
-
-
8.5
-
-
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pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5
8
-
pH 5: 16% of the activity, pH 8: 80% of the activity
6.8
8.2
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HEPES buffer
7
8.5
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using 4-nitrophenyl acetate as substrate
7
-
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60% lower activity compared to optimum
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-
substrate 4-nitrophenyl acetate, wild-type SsNeuA and mutant SsNeuA234-410
25
-
-
assay at
37
-
-
assay at
37
-
-
assay at
pI VALUE
pI VALUE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4.8
-
-
isoelectric focusing, low pI form
5.7
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-
isoelectric focusing, high pI form
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
-
catalytic regulation of B cell receptor (BCR) signalling and B-cell development, knockout mice: striking decrease in number of splenic marginal zone B-cells and marginal zone B-cell precursors, reduced number in follicular B-cells, loss of recirculating B-cells in bone marrow, lymphocyte-intrinsic defects
Manually annotated by BRENDA team
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restricted distribution, strongest expression of the lysosomal enzyme
Manually annotated by BRENDA team
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almost exclusively the nonglycosylated form of the enzyme
Manually annotated by BRENDA team
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high levels of activity of both forms of the enzyme, nonglycosylated and glycosylated
Manually annotated by BRENDA team
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hepatoietic cell line
Manually annotated by BRENDA team
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almost exclusively the nonglycosylated form of the enzyme
Manually annotated by BRENDA team
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high levels of activity of both forms, nonglycosylated and glycosylated
Manually annotated by BRENDA team
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restricted distribution, strongest expression of the lysosomal enzyme
Manually annotated by BRENDA team
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acetone powder, equal amounts of the glycosylated and nonglycosylated form of the enzyme
Manually annotated by BRENDA team
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acetone powder of the glycosylated form of the enzyme
Manually annotated by BRENDA team
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normal and cancer mucosa
Manually annotated by BRENDA team
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restricted distribution, strongest expression of the lysosomal enzyme
Manually annotated by BRENDA team
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only the glycosylated form of the enzyme
Manually annotated by BRENDA team
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high levels of activity of both forms, nonglycosylated and glycosylated
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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isoform Lse, secreted from post-Golgi vesicle, limited lysosomal localisation
Manually annotated by BRENDA team
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only little activity
-
Manually annotated by BRENDA team
additional information
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multiple transcript variants of this gene encode different isoforms, found either in the lysosome or in the cytosol. The variant 1 represents the shorter transcript but encodes the longer protein, isoform 1, referred to as the lysosomal form of the protein. The variant 2 differs in the 5' UTR and coding region compared to transcript variant 1. The resulting protein, isoform 2, has a distinct N-terminus and is also referred as the cytosolic form of the protein
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Manually annotated by BRENDA team
additional information
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the cytosolic and lysomomal form of the enzyme are found in very different subcellular compartments, but they are encoded by a single gene by different usage of a signal peptide-encoding exon at the N terminus
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Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
Bovine coronavirus (strain Mebus)
Bovine coronavirus (strain Mebus)
Influenza C virus (strain C/Johannesburg/1/1966)
Murine coronavirus (strain S)
Murine coronavirus (strain S)
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
37230
-
-
MALDI-TOF mass spectrometry
37700
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theoretical
40000
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SDS-PAGE, purified, recombinant protein
54000
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gel-filtration
56500
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gel filtration and SDS-PAGE
56500
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gel filtration
60000
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gel filtration
61000
-
-
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62800
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gel filtration
80000
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SDS PAGE under non-reducing conditions
88000
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gel fitration
250000
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nonreducing PAGE, equal MW for both the larger and smaller Lse subunit, expressed in COS-7 cells
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
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two forms with molecular weights of 75000 and 88000 Da detected in SDS-PAGE, the 75000 Da form is assumed to by the unglycosylated precursor of the enzyme
?
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x * 75000, nonreducing SDS-PAGE
?
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x * 52000, glycoprotein, after treatment with endo-beta-N-acetylglycosaminidase H and peptide:N-glycosidase F; x * 65000, linked to a N-oligosaccharides
dimer
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1 * 29000 + 1 * 36000, SDS-PAGE
dimer
P15776
crystal structure, disulphide-linkage through Cys385, 2fold crystallographic symmetry
dimer
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1 * 30000 + 1 * 65000, SDS-PAGE
dimer
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1 * 57000 + 1* 24000, SDS-PAGE
dimer
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1 * 38000 + 1 * 28000, SDS-PAGE
dimer
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1 * 36400 + 1* 30300, SDS-PAGE
dimer
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1 * 30000 + 1 * 36000
dimer
influenza C virus Johannesburg/1/66
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1 * 57000 + 1* 24000, SDS-PAGE
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monomer
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by gel filtration and dynamic light scattering, NanS adopts a SGNH hydrolase fold. The monomer has a central seven-stranded mixed beta-sheet with a strand order of beta5, beta2, beta6, beta1, beta9, beta10, beta11. Additionally, two beta-hairpins are present following strands beta2 and beta6. The N- and C-terminal alpha-helices, alpha1 and alpha7 respectively, are situated on the concave side of the beta-sheet while the remaining alpha-helices (alpha2, alpha4, and alpha6) are positioned on the convex side with alpha3 and alpha5 being one-turn 310-helices. Several extended loops are present on the concave side of the beta-sheet. One solvent exposed loop, Asn216-Thr218, located between alpha4 and beta6 is disordered in the structure
monomer
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1* 56500, gel filtration and SDS-PAGE
additional information
-
SsNeuA is cleaved into two fragments, in which the 29-kDa protein recovers from SDS-PAGE still remaining its O-acetylesterase activity. The esterase domain is composed of 177 amino acid residues at C-terminal of the SsNeuA and its activity does not structurally depend on the CMP-Neu5Ac synthetase domain, overview
additional information
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sequence motifs and two subfamilies of SGNH hydrolases, overview
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
glycoprotein
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purified, recombinant protein, deglycosylation with N-glycosidase F
glycoprotein
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side-chain modification
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glycoprotein, Lse
side-chain modification
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side-chain modification
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glycoprotein, linked with N-oligosaccharides, LSE, cleaved by endo-beta-N-acetylglycosaminidase H and peptide:N-glycosidase F
side-chain modification
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contains N-linked oligosaccarides, after treatment with peptide N-glycosidase decrease of 10000 Da in the apparent molecular weight, endoglycosidase H causes a much smaller shift; glycoprotein, linked with N-oligosaccharides, LSE, cleaved by endo-beta-N-acetylglycosaminidase H and peptide:N-glycosidase F
side-chain modification
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glycoprotein, partly resistant to endo-beta-N-acetylglycosaminidase H, but sensitive to peptide N-glycosidase
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
apo-enzyme (PDB: 3CL4) or mutant S40A in complex with 5-N-acetyl-4,9-di-O-acetylneuraminic acid alpha-methylglycoside (PDB: 3CL5), hanging drop vapour diffusion, 18C, 2 weeks, precipitant: 16% polyethylene glycol 8000 and 20% glycerol or 10% polyethylene glycol 3350, hexagonal bipyramide crystals: space groups: P6(5)22, unit cell parameter: a, b: 88.8-89.3, c: 280.4-282.4, soaking with 7 mM 5-N-acetyl-4,9-di-O-acetylneuraminic acid alpha-methylglycoside, molecular replacement using PDB: 1FLC (for apo-enzyme) or wild-type structure (for S40A mutant) as template, three domains: receptor-binding domain (R), acetylase domain (E, strictly conserved), and membrane-proximal domain (MP), homodimer of 2fold crystallographic symmetry with 2 major contact regions (CR1: bridges R domains, CR2: involves MP), disorder of residues 377-388, E-domain: SGNH-hydrolase fold, active site with catalytic triad (Ser40, His329, Asp326) and oxyanion hole (Asn104, Ser40, Gly75), highly variable surface loop (residues 47-54) is site of antigenic variation, R-domain: different from those of hemagglutinin-esterase fusion (HEF) and agglutinin (HA) (plasticity), binding of ligand in opposite orientation involving residues Leu212, Asn214, Ser213, Tyr184, Phe211, Leu266, Leu267 (hydrophobic pocket), coordination of potassium and water by Asp220, Ser221, Gln222, Ser263, Glu265, Leu267
P15776
purified wild-type apo-NanS and SeMet-labeled NanS, mixing of 0.001 ml of protein in the final buffer with 0.001 ml of reservoir solution containing 0.2 M NaCl, 0.1 M Bis-Tris pH 5.5, 30% w/v PEG 3350, in micro batch experiments under oil, X-ray diffraction structure determination and analysis at 1.6-2.2 A resolution
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molecular modelling using PDB: 1FLC, and alpha-methyl or beta-methyl glycosides of 9-acetamido-9-deoxy-N-acetylneuraminic acid or N-acetyl-9-O-acetyl-2,6-alpha-S-glucosyl-neuraminic acid alpha-methylglycoside as substrates, no interaction between aglycon moiety and the enzyme or its active site, catalytic triad: Ser57, His355, Asp352, catalysis involves conformational change of Ser57 side chain in order to enable 9-O-acetyl-binding and position for nucleophilic attack on 9-O-acetate carbonyl carbon, beta-anomer substrate lacks bi-dendate interaction between C-1 carboxylate group and Asp352 and is no suitable substrate
P07975
the inhibitor 2-alpha-thiomethylmercuryl 9-acetamido-9-deoxy sialoside is used to prepare heavy atom derivatives of the crystals
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TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
25
-
-
room temperature, complete inactivation in the presence of 10 mM 2-mercaptoethanol after 8 h
37
-
-
40% activity is lost in 20 h
96
-
-
in the presence of bovine serum albumin, loss of activity within 1 min
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
partially purified esterase (from second ion exchange chromatography) resistant to freezing-thawing cycles, presence of beta-mercaptoethanol during purification preserves enzyme activity
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activity becomes unstable on excessive dilution
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lyophilization and reconstitution results in loss of 30% of activity
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single cycle of freeze-thaw results in little loss of activity, repeated freeze-thaw results in gradual loss of activity
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OXIDATION STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
15 min incubation with 1 mM 4-hydroxymercuribenzoate at 25C leads to total loss of activity
-
698132
contains disulfide bonds
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701059
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, after preparative isoelectric focusing, few weeks, total loss of activity, -70C, frozen liver, stable for 1-2 years
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-20C, 20 mM HEPES 150 mM NaCl pH 8, 3 weeks, fully active
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4C, 20 mM HEPES 150 mM NaCl pH 8, 1 week, fully active
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-80C, in lyophilized form, no loss of activity
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37C, in the presence of bovine serum albumin, decrease of 50% of the activity within 2 h
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4C, Tris-HCl, pH7.8, 2 mM mercaptoethanol, 90% loss of activity after 1 day, addition of 15 mM bovine serum albumin prevents loss during 7 days
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4C, concentrated purified enzyme, stable for at least 1 month
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Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
separated from alpha-L-arabinofuranosidase and alpha-L-rhamnopyranosidase in commercial enzyme preparations
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2600fold enrichment
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from HEK293S cells by protein A-affinity chromatography followed by on-bead thrombin digestion
P15776
850fold enrichment
-
from fresh tissue by ultracentrifugation (dialysis of supernatant), followed by gel-filtration on Sephadex G-200 column, ion-exchange chromatography on Sephadex-DEAE-A-50 column, second ion-exchange chromatography on DEAE-Sephacel column, isoelectric focussing on ampholine of pH 3.5-9.5 and a saccharose gradient, and final dialysis, 866% purification compared to homogenate
-
nickel-affinity chromatography, elution with 500 mM imidazole, pH 7.5, yield of 300 microg soluble recombinant protein per litre Sf9 cell culture (3 mg/l insoluble)
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180fold enrichment
-
from baculovirus infected insect Sf9 cells as GFP-fusion protein by ultracentrifugation, ion-exchange chromatography on Q-Sepharose FF column and dialysis
P07975
copurified with a 66000 Da esterase
-
nickelnitrilotriacetic acid-agarose chromatography
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Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
sequence encoding ectodomain (residues 19-388) in plasmid pCD5-BCoVHE-T-Fc for expression with N-terminal CD5 signal peptide and C-terminal thrombin cleavage site followed by human IgG1 Fc domain in N-acetylglucosaminyltransferase-deficient HEK293S cells
P15776
in pBACgus-6, -3, -1 for baculovirus-mediated expression for 4 h at 20C with C-terminal hexa-His-tag in insect Sf9 cells, deletion of transmembrane region and cytoplasmic tail
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expressed as GFP-fused secretion protein in Sf9 cells
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expressed in COS-7 cells, both the larger and smaller Lse subunit
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expression in E. coli BL21
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expression of wild-type and mutant enzymes in Escherichia coli BL21(DE3). SsneuA can restore both CMP-Neu5Ac synthetase and O-acetylesterase activities in complemented enzyme-deficient Escherichia coli strains, but the activities in the complemented strain are different from those in the wild-type Escherichia coli strain. However, the Streptococcus suis O-acetylesterase domain alone is unable to act on intracellular O-acetyl-Neu5Ac in Escherichia coli
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EXPRESSION
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expression of lysosomal and cytosolic form of SIAE is significantly downregulated both in lymphoblasts of acute lymphoblastic leukemia patients and acute lymphoblastic leukemia-cell line in comparison to peripheral blood mononuclear cells from healthy donors, semi-quantitative RT-PCR using specific primers for both SIAE genes, overview
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ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
F211A
P15776
abrogated ligand recognition and binding
L266A
P15776
abrogated ligand recognition and binding
L267A
P15776
abrogated ligand recognition and binding
S40A
P15776
catalytically inactive, active site residue, retained lectin activity
Y184A
P15776
decreased ligand binding affinity
E26A
-
site-directed mutagenesis, the mutant shows highly reduced activity compared to the wild-type NanS
H301N
-
site-directed mutagenesis, inactive mutant
S19A
-
site-directed mutagenesis, inactive mutant
S300A
-
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type NanS
T294A
-
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type NanS
T294S
-
site-directed mutagenesis, the mutant shows reduced activity compared to the wild-type NanS
S258A
-
site-directed mutagenesis
S57T
-
loss of esterase activity
additional information
-
construction of recombinant MHV-A59 derivatives in which the autologous genes for hemagglutinin-esterase and sialidase are replaced by those of MHV-S or MHV-DVIM by targeted RNA recombination. The mutants do not express functional hemagglutinin-esterase, in MHV-A59, the hemagglutinin-esterase gene is interrupted by a nonsense mutation at codon 15 and that consequently MHV-A59 and derivates rMHV-A59-SDVIM and rMHV-A59-SS do not express the hemagglutinin-esterase protein
additional information
-
the mutant SsNeuAs truncated from 166 to 233 amino acids at the N-terminal a re active for pNP-Ac and their esterase activities are almost the same as the wild-type, only with one exception of the SsNeuA167-410, while the mutant SsNeuAs terminated at amino acid position of 227, 232, 233, 241, 247, 267, 283, 293, 312, 322, 338, 355 and 377 are inactive in CMP-Neu5Ac synthetase activity, even removal of 33 amino acid residues at C-terminal of the SsNeuA leads to a complete loss of CMP-Neu5Ac synthetase activity
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
drug development
-
drug design, two essential pharmacophoric groups of ligand: 9-O-acetyl group and C-1 carboxylate group, anti-virus infection
drug development
P15776
broad-spectrum antivirals that target orthomyxo- and coronavirus sialate-O-acetylesterases
molecular biology
P15776
origin and evolution of viral hemagglutinin-esterases
drug development
bovine coronavirus BcoV
-
drug design, two essential pharmacophoric groups of ligand: 9-O-acetyl group and C-1 carboxylate group, anti-virus infection
-
analysis
-
detection of 9-O-acetylated sialic acids on sialoglycoconjugates immobilized on microtiter plates, nitrocellulose or separated on thin-layer chromatograms. The assay takes advantage of two different biological properties of influenza C virus, its high affinity-binding to 9-O-acetylated sialic acids and its sialate 9-O-acteylesterase that is used for detection of bound virus
drug development
P07975
drug design, two essential pharmacophoric groups of ligand: 9-O-acetyl group and C-1 carboxylate group, anti-virus infection
drug development
influenza C virus INF-C
-
drug design, two essential pharmacophoric groups of ligand: 9-O-acetyl group and C-1 carboxylate group, anti-virus infection
-