Information on EC 2.6.1.50 - glutamine-scyllo-inositol transaminase

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The expected taxonomic range for this enzyme is: Bacteria

EC NUMBER
COMMENTARY
2.6.1.50
-
RECOMMENDED NAME
GeneOntology No.
glutamine-scyllo-inositol transaminase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone = 2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
A pyridoxal-phosphate protein
-
-
-
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone = 2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
mechanism, enzyme distinguishes the enantiotopic amino groups of 2-deoxystreptamine but accepts both enantiomers of 2-deoxy-scyllo-inosose to give a racemic product
-
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone = 2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
mechanism, enzyme distinguishes the enantiotopic amino groups of 2-deoxystreptamine but accepts both enantiomers of 2-deoxy-scyllo-inosose to give a racemic product
Bacillus circulans SANK 72073
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
amino group transfer
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
Streptomycin biosynthesis
-
streptomycin biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
L-glutamine:2,4,6/3,5-pentahydroxycyclohexanone aminotransferase
A pyridoxal-phosphate protein.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
aminocyclitol aminotransferase
-
-
glutamine scyllo-inosose aminotransferase
-
-
-
-
glutamine-scyllo-inosose aminotransferase
-
-
-
-
L-glutamine-keto-scyllo-inositol aminotransferase
-
-
-
-
L-glutamine-scyllo-inosose transaminase
-
-
-
-
L-glutamine:2-deoxy-scyllo-inosose
Q53U20
-
L-glutamine:2-deoxy-scyllo-inosose
Streptomyces fradiae IFO12773, Streptomyces fradiae IFO13147
Q53U20
-
-
L-glutamine:2-deoxy-scyllo-inosose aminotransferase
Q53U20
-
L-glutamine:inosose aminotransferase
-
-
neo-6
Q53U20
-
neo-6
Streptomyces fradiae NCIMB 8233
Q53U20
-
-
CAS REGISTRY NUMBER
COMMENTARY
9033-03-8
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
strain SANK 72073
-
-
Manually annotated by BRENDA team
Bacillus circulans SANK 72073
strain SANK 72073
-
-
Manually annotated by BRENDA team
no activity in Escherichia coli
host strain, free of enzymatic activity
-
-
Manually annotated by BRENDA team
no activity in Streptomyces lividans
66 strain 1326; 66 strain TK23, host strains, free of enzymatic activity
-
-
Manually annotated by BRENDA team
expression in Escherichia coli
-
-
Manually annotated by BRENDA team
Streptomyces bikiniensis NRRL 1049b
NRRL 1049b
-
-
Manually annotated by BRENDA team
IFO12773, nucleotide sequence deposited with the same accession number in EMBL/GenBank; IFO 13147, nucleotide sequence deposited with the same accession number in EMBL/GenBank
SwissProt
Manually annotated by BRENDA team
strain NCIMB 8233, overexpression in Escherichia coli
SwissProt
Manually annotated by BRENDA team
Streptomyces fradiae NCIMB 8233
strain NCIMB 8233, overexpression in Escherichia coli
SwissProt
Manually annotated by BRENDA team
ATCC 12475
-
-
Manually annotated by BRENDA team
N2-3-11, DSM 40236
-
-
Manually annotated by BRENDA team
subsp. glebosus ATCC 14607
-
-
Manually annotated by BRENDA team
subsp. glebosus DSM 40823
-
-
Manually annotated by BRENDA team
JCM4433, nucleotide sequence deposited with the same accession number in EMBL/GenBank
SwissProt
Manually annotated by BRENDA team
ATCC 23265
-
-
Manually annotated by BRENDA team
JCM4923, nucleotide sequence deposited with the same accession number in EMBL/GenBank
SwissProt
Manually annotated by BRENDA team
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-scyllo-inosose + L-glutamine
2-deoxy-scyllo-inosamine + 2-ketoglutaramate
show the reaction diagram
Q53U20, -
-
-
-
?
2-deoxy-scyllo-inosose + L-glutamine
2-deoxy-scyllo-inosamine + 2-ketoglutaramate
show the reaction diagram
-
-, tbmB catalyzes the second step of the DOS biosynthetic pathway during the biosynthesis of 2-deoxystreptamine, a subunit of tobramycin, in Streptomyces tenebrarius
-
-
?
2-deoxy-scyllo-inosose + L-glutamine
2-deoxy-scyllo-inosamine + 2-ketoglutaramate
show the reaction diagram
Streptomyces fradiae NCIMB 8233
Q53U20
-
-
-
?
2-deoxy-scyllo-inosose + L-glutamine
2-deoxy-scyllo-inosamine + 2-oxoglutarate
show the reaction diagram
Bacillus circulans, Bacillus circulans SANK 72073
-
accepts both enantiomers to give a racemic product
-
-
r
2-deoxy-scyllo-inosose + L-glutamine
2-deoxy-scyllo-inosamine + 2-oxoglutaramate
show the reaction diagram
-
-
-
-
?
2-deoxystreptamine + 2-ketoglutaramate
2-deoxy-keto-inosamine + L-glutamine
show the reaction diagram
-
-
-
r
2-deoxystreptamine + 2-oxoglutaramate
2-deoxy-scyllo-inositol + L-glutamine
show the reaction diagram
-
-
-
-
r
2-deoxystreptamine + keto-scyllo-inositol
2-deoxy-scyllo-inositol + amino-deoxy-keto-scyllo-inositol
show the reaction diagram
-
-
-
-
r
2-deoxystreptamine + pyruvate
2-keto-inosose + L-alanine
show the reaction diagram
Q53U20, -
-
-
-
r
2-deoxystreptamine + pyruvate
2-keto-inosose + L-alanine
show the reaction diagram
Streptomyces fradiae NCIMB 8233
Q53U20
-
-
-
r
aminodeoxy-scyllo-inositol + 2-oxoglutaramate
scyllo-inositol + L-glutamine
show the reaction diagram
-
-
-
-
r
aminodeoxy-scyllo-inositol + keto-scyllo-inositol
amino-scyllo-inositol + aminodeoxy-keto-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 1D-4-keto-myo-inositol
2-oxoglutaramate + amino-deoxy-1D-4-keto-myo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
keto-scyllo-inositol
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
streptidine subpathway of streptomycin biosynthesis
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
2-deoxystreptamine biosynthesis
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
Streptomyces bikiniensis NRRL 1049b
-
-
-
-
r
L-glutamine + 2-oxoadipate
2-oxoglutaramate + L-2-amino-1,6-hexandioate
show the reaction diagram
-
-
-
-
r
L-glutamine + 2-oxobutyrate
2-oxoglutaramate + 2-aminobutyrate
show the reaction diagram
-
-
-
-
r
L-glutamine + 2-oxocaproate
2-oxoglutaramate + L-norleucine
show the reaction diagram
-
-
-
-
r
L-glutamine + 2-oxoglutaramate
2-oxoglutaramate + L-glutamine
show the reaction diagram
-
-
-
-
r
L-glutamine + 2-oxoglutarate
2-oxoglutaramate + L-glutamate
show the reaction diagram
-
-
-
-
r
L-glutamine + 2-oxoglutarate
2-oxoglutaramate + L-glutamate
show the reaction diagram
-
-
-
-
r
L-glutamine + 2-oxovalerate
2-oxoglutaramate + L-norvaline
show the reaction diagram
-
-
-
-
r
L-glutamine + DL-epi-inosose
2-oxoglutaramate + amino-deoxy-inosose
show the reaction diagram
-
-
-
-
r
L-glutamine + glyoxalate
2-oxoglutaramate + glycine
show the reaction diagram
-
-
-
-
r
L-glutamine + oxaloacetate
2-oxoglutaramate + L-aspartate
show the reaction diagram
-
-
-
-
r
L-glutamine + pyruvate
2-oxoglutaramate + L-alanine
show the reaction diagram
-
-
-
-
r
L-glutamine + pyruvate
2-oxoglutaramate + L-alanine
show the reaction diagram
-
-
-
-
r
myo-inositol + diaminocyclitol + oxaloacetate
amino-deoxyinositol + ketoaminocyclitol + malate
show the reaction diagram
-
-
-
-
r
myo-inositol + glutamine + oxalacetate
amino-deoxyinositol + 2-oxoglutarate + malate + NH4+
show the reaction diagram
-
-
-
-
r
N3-methyl-2-deoxy-streptamine + inosose
aminodeoxyinositol + 1-keto-2-deoxy-3-methylaminodeoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
N3-methyl-2-deoxy-streptamine + keto-scyllo-inositol
3-methylamino-2-deoxy-scyllo-inositol + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
N3-methyl-2-deoxystreptamine + 2-oxoglutaramate
3-methylamino-2-deoxy-scyllo-inositol + L-glutamine
show the reaction diagram
-
-
-
-
r
scyllo-inosose + L-glutamine
scyllo-inosamine + 2-oxoglutaramate
show the reaction diagram
-
-
-
-
?
streptamine + 2-oxoglutaramate
amino-scyllo-inositol + L-glutamine
show the reaction diagram
-
-
-
-
r
streptamine + keto-scyllo-inositol
amino-scyllo-inositol + amino-deoxy-keto-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + scyllo-inosose
scyllo-inosamine + 2-oxoglutaramate
show the reaction diagram
-
-
spontaneously cyclization of 2-oxoglutaramate to 2-pyrrolidone-5-hydroxy-5-carboxylic acid
r
additional information
?
-
-
enzyme is also involved in transamination of a putative aminoketone intermediate in 2-deoxystreptamine synthesis
-
-
-
additional information
?
-
Q53U20
the enzyme is responsible for 2-deoxystreptamine production
-
-
-
additional information
?
-
Bacillus circulans SANK 72073
-
enzyme is also involved in transamination of a putative aminoketone intermediate in 2-deoxystreptamine synthesis
-
-
-
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
2-deoxy-scyllo-inosose + L-glutamine
2-deoxy-scyllo-inosamine + 2-ketoglutaramate
show the reaction diagram
-
tbmB catalyzes the second step of the DOS biosynthetic pathway during the biosynthesis of 2-deoxystreptamine, a subunit of tobramycin, in Streptomyces tenebrarius
-
-
?
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
-
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
streptidine subpathway of streptomycin biosynthesis
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
-
2-deoxystreptamine biosynthesis
-
-
r
L-glutamine + 2,4,6/3,5-pentahydroxycyclohexanone
2-oxoglutaramate + 1-amino-1-deoxy-scyllo-inositol
show the reaction diagram
Streptomyces bikiniensis NRRL 1049b
-
-
-
-
r
additional information
?
-
Bacillus circulans, Bacillus circulans SANK 72073
-
enzyme is also involved in transamination of a putative aminoketone intermediate in 2-deoxystreptamine synthesis
-
-
-
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
pyridoxal 5'-phosphate
-
-
pyridoxal 5'-phosphate
-
-
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
5,5'-dithio-bis(2-nitrobenzoic acid)
-
reduces specific activity by 50%
p-hydroxymercuribenzoate
-
reduces specific activity by 50%
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
45500
-
-
SDS-PAGE
64000
76000
-
gel filtration
95000
100000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
Q53U20
x * 46951, His6-tagged protein, claculated, x * 45000, His6-tagged protein, SDS-PAGE
?
Streptomyces fradiae NCIMB 8233
-
x * 46951, His6-tagged protein, claculated, x * 45000, His6-tagged protein, SDS-PAGE
-
dimer
-
2 * 45000, SDS-PAGE
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
50
-
-
heat labile, loses all activity upon incubation for 20 min
55
-
-
relatively resistant to heating for 5 min
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
activity rapidly lost when dialyzed
-
pyridoxal 5'-phosphate or pyruvate stabilizes during dialysis
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20°C, stored at concentrations greater than 1mg/ml, stable for several months with little loss of activity
-
4°C, inactivated within 1 month
-
6°C, purified enzyme stable for several weeks
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
recombinant enzyme, pJAW76-2, expressed in Streptomyces lividans
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
btrS gene identified and heterologously expressed
-
expressed heterologously in Escherichia coli
-
; btrS homologous gene identified and sequenced
Q53U20
the gene is cloned into pIBR25, a Streptomyces expression vector and transformed into a non-aminoglycoside-producing host, Streptomyces venezuelae YJ003, for heterologous expression
Q53U20
gene StsC identified, cloned by PCR and expressed in Escherichia coli BL21 and Streptomyces lividans
-
btrS homologous gene identified and sequenced
Q6F6I1
btrS homologous gene identified and sequenced
Q4R0W2
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
pharmacology
-
2-deoxystreptamine is a component of numerous clinically important antibiotics such as gentamicin, neomycin, tobramycin, amikacin and hygromycin
pharmacology
Q53U20
biosynthesis of aminoglycoside antibiotics
pharmacology
Streptomyces fradiae IFO12773, Streptomyces fradiae IFO13147
-
biosynthesis of aminoglycoside antibiotics
-
pharmacology
-
5'-hydroxystreptomycin production
pharmacology
-
spectinomycin production