Information on EC 2.4.1.56 - lipopolysaccharide N-acetylglucosaminyltransferase

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The expected taxonomic range for this enzyme is: Proteobacteria

EC NUMBER
COMMENTARY
2.4.1.56
-
RECOMMENDED NAME
GeneOntology No.
lipopolysaccharide N-acetylglucosaminyltransferase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
UDP-N-acetyl-alpha-D-glucosamine + lipopolysaccharide = UDP + N-acetyl-alpha-D-glucosaminyllipopolysaccharide
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
hexosyl group transfer
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Lipopolysaccharide biosynthesis
-
Metabolic pathways
-
SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-D-glucosamine:lipopolysaccharide N-acetyl-D-glucosaminyltransferase
Transfers N-acetylglucosaminyl residues to a D-galactose residue in the partially completed lipopolysaccharide core [cf. EC 2.4.1.44 (lipopolysaccharide 3-alpha-galactosyltransferase), EC 2.4.1.58 (lipopolysaccharide glucosyltransferase I) and EC 2.4.1.73 (lipopolysaccharide glucosyltransferase II)].
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
acetylglucosaminyltransferase, uridine diphosphoacetylglucosamine-lipopolysaccharide
-
-
-
-
bifunctional glycosyltransferase
-
-
N-acetylglucosamine glycosyltransferase
-
-
-
-
N-acetylglucosaminyltransferase
-
-
UDP-N-acetylglucosamine-lipopolysaccharide N-acetylglucosaminyltransferase
-
-
-
-
uridine diphosphoacetylglucosamine-lipopolysaccharide acetylglucosaminyltransferase
-
-
-
-
WahA glycosyltransferase
-
-
CAS REGISTRY NUMBER
COMMENTARY
37277-64-8
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
strains 35000HP and 35000HP-RSM212
-
-
Manually annotated by BRENDA team
obligate human pathogen; strain H44/76, immunotype L3; strains M981, NMB
-
-
Manually annotated by BRENDA team
strain H44/76, immunotype L3
-
-
Manually annotated by BRENDA team
strain H44/76, immunotype L3
-
-
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
UDP-N-acetyl-D-galactosamine + lipooligosacccharide
UDP + N-acetyl-D-galactosaminyllipooligosaccharide
show the reaction diagram
-
76% of activity with UDP-N-acetyl-D-glucosamine, 10fold lower affinity than for UDP-N-acetyl-D-glucosamine, beta1-3-linkage of N-acetyl-D-galactosamine to accepting Gal residues
-
-
?
UDP-N-acetyl-D-glucosamine + beta-D-Galp-(1-4)-beta-D-Glcp-O-(CH2)6-NH-dansyl
?
show the reaction diagram
-
-
-
-
?
UDP-N-acetyl-D-glucosamine + Galbeta1-3GalNAcbeta-O-p-nitrophenol
UDP + GlcNAcbeta-1-3Galbeta1-3GalNAcbeta-O-p-nitrophenol
show the reaction diagram
-
low affinity
-
-
?
UDP-N-acetyl-D-glucosamine + Galbeta1-4Glc lipooligosaccharide
UDP + GlcNAcbeta1-3Galbeta1-4Glc lipooligosaccharide
show the reaction diagram
-
low affinity
-
-
?
UDP-N-acetyl-D-glucosamine + Galbeta1-4Glcbeta-O-p-nitrophenol
UDP + GlcNAcbeta1-3Galbeta1-4Glcbeta-O-p-nitrophenol
show the reaction diagram
-
-
-
-
?
UDP-N-acetyl-D-glucosamine + Galbeta1-4GlcNAcbeta-O-p-nitrophenol
UDP + GlcNAcbeta1-3-Galbeta1-4GlcNAcbeta-O-p-nitrophenol
show the reaction diagram
-
-
-
-
?
UDP-N-acetyl-D-glucosamine + lactose
UDP + N-acetyl-D-glucosaminyllactose
show the reaction diagram
-
lactose is the highly preferred acceptor substrate
-
-
?
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
-
-
-
?
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosacccharide, terminal Gal is an absolute acceptor requirement, broad acceptor specificity toward both alpha- and beta-galactosides structurally related to N- or O-protein or lipid-linked oligosaccharides, beta1-3-linkage of N-acetyl-D-glucosamine to accepting Gal residues in the extending lipooligosacccharide, lactose is the highly preferred acceptor substrate, enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine
-
-
?
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
transfers N-acetylglucosamine to lipooligosaccharides, structure of the lipooligosaccharide
-
-
-
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
transfers N-acetylglucosamine to lipooligosaccharides, structure of the lipooligosaccharide
-
-
-
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosacccharide, lactose is the natural acceptor disaccharide sequence in lipooligosaccharide
-
-
?
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosacccharide, terminal Gal is an absolute acceptor requirement, broad acceptor specificity toward both alpha- and beta-galactosides structurally related to N- or O-protein or lipid-linked oligosaccharides, beta1-3-linkage of N-acetyl-D-glucosamine to accepting Gal residues in the extending lipooligosacccharide, lactose is the highly preferred acceptor substrate, enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine, involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosacccharide, lactose is the natural acceptor disaccharide sequence in lipooligosaccharide
-
-
?
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
transfers N-acetylglucosamine to lipooligosaccharides, structure of the lipooligosaccharide
-
-
-
UDP-N-acetyl-D-glucosamine + lipopolysaccharide
UDP + N-acetyl-D-glucosaminyllipopolysaccharide
show the reaction diagram
-
-
-
?
UDP-N-acetyl-D-glucosamine + lipopolysaccharide
UDP + N-acetyl-D-glucosaminyllipopolysaccharide
show the reaction diagram
-
involved in synthesis of cell wall lipopolysaccharides, transfers N-acetylglucosaminyl residues to a D-glucose residue in the partially completed lipopolysaccharide core, the results are consistent with the postulated attachment of N-acetylglucosamine to glucose, but do not exclude linkage to another residue
-
-
?
UDP-N-acetyl-D-glucosamine + lipopolysaccharide
?
show the reaction diagram
-
-
-
-
?
UDP-N-acetyl-D-glucosamine + N-acetyllactosamine
UDP + N-acetyl-D-glucosaminyl-N-acetyllactosamine
show the reaction diagram
-
enzyme also acts efficiently on monomeric and dimeric N-acetyllactosamine
-
-
?
additional information
?
-
-
different genes lgtA and rfaK encode enzymes which transfer N-acetylglucosamine to lipooligosaccharides, lgtA: beta-1,3-N-acetylglucosamine transferase, rfaK: alpha-1,2-N-acetylglucosamine transferase
-
-
-
additional information
?
-
-
no sugar donors: UDPglucose, UDPgalactose, UDPglucosamine, overview over oligosaccharide acceptor specificity
-
-
-
additional information
?
-
-
involved in synthesis of glycoforms of lipooligosaccharide: synthesis of the A-branch and B-branch
-
-
-
additional information
?
-
-
inner-core biosynthesis of lipooligosaccharide, an outer membrane glycolipid
-
-
-
additional information
?
-
-
synthesized donor substrates methyl-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-diphosphate, benzyl-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-diphosphate, 4-phenylbutyl-(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)-diphosphate and 2-acetamido-2-deoxy-alpha-D-glucopyranose 1-diphosphate show no reactivity
-
-
-
additional information
?
-
-
no sugar donors: UDPglucose, UDPgalactose, UDPglucosamine, overview over oligosaccharide acceptor specificity
-
-
-
additional information
?
-
-
different genes lgtA and rfaK encode enzymes which transfer N-acetylglucosamine to lipooligosaccharides, lgtA: beta-1,3-N-acetylglucosamine transferase, rfaK: alpha-1,2-N-acetylglucosamine transferase, inner-core biosynthesis of lipooligosaccharide, an outer membrane glycolipid
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-
-
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
UDP-N-acetyl-D-glucosamine + lipooligosacccharide
UDP + N-acetyl-D-glucosaminyllipooligosaccharide
show the reaction diagram
-
involved in the synthesis of the lacto-N-neo-tetraose structural element of the bacterial lipooligosacccharide, lactose is the natural acceptor disaccharide sequence in lipooligosaccharide
-
-
?
UDP-N-acetyl-D-glucosamine + lipopolysaccharide
UDP + N-acetyl-D-glucosaminyllipopolysaccharide
show the reaction diagram
-
involved in synthesis of cell wall lipopolysaccharides, transfers N-acetylglucosaminyl residues to a D-glucose residue in the partially completed lipopolysaccharide core, the results are consistent with the postulated attachment of N-acetylglucosamine to glucose, but do not exclude linkage to another residue
-
-
?
additional information
?
-
-
involved in synthesis of glycoforms of lipooligosaccharide: synthesis of the A-branch and B-branch
-
-
-
additional information
?
-
-
inner-core biosynthesis of lipooligosaccharide, an outer membrane glycolipid
-
-
-
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Fe2+
-
activates, less effective than Mn2+
Mg2+
-
activates, less effective than Mn2+
Mn2+
-
absolute requirement for divalent cations of which Mn2+ is most active, optimal concentration: 15 mM
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
UDP
-
1.5 mM: 50% inhibition
2-acetamido-2-deoxy-alpha-D-glucopyranosyl 1-diphosphate
-
-
additional information
-
not inhibited by UMP
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
27
-
Galbeta1-3GalNAcbeta-O-p-nitrophenol lipooligosaccharide
-
UDP-N-acetyl-D-glucosamine as donor
-
28
-
Galbeta1-4Glc lipooligosaccharide
-
UDP-N-acetyl-D-glucosamine as donor
-
36
-
Galbeta1-4Glc lipooligosaccharide
-
UDP-N-acetyl-D-galactosamine as donor
-
4.3
-
Galbeta1-4Glcbeta-O-p-nitrophenol lipooligosaccharide
-
UDP-N-acetyl-D-glucosamine as donor
-
4.5
-
Galbeta1-4Glcbeta-O-p-nitrophenol lipooligosaccharide
-
UDP-N-acetyl-D-galactosamine as donor
-
6.1
-
Galbeta1-4GlcNAcbeta-O-p-nitrophenol lipooligosaccharide
-
UDP-N-acetyl-D-glucosamine as donor
-
7.2
-
Galbeta1-4GlcNAcbeta-O-p-nitrophenol lipooligosaccharide
-
UDP-N-acetyl-D-galactosamine as donor
-
0.016
-
lipopolysaccharide
-
-
0.052
-
lipopolysaccharide
-
mutants with recombinant plasmids expression of C- or N-domains
2.4
-
UDP-N-acetyl-D-galactosamine
-
-
0.04
-
UDP-N-acetyl-D-glucosamine
-
-
0.119
-
UDP-N-acetyl-D-glucosamine
-
mutants with recombinant plasmids expression of C- or N-domains
0.22
-
UDP-N-acetyl-D-glucosamine
-
-
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2.5
-
lipopolysaccharide
-
mutants with recombinant plasmids expression of C- or N-domains
30076
25
-
lipopolysaccharide
-
-
30076
1
-
UDP-N-acetyl-D-glucosamine
-
mutants with recombinant plasmids expression of C- or N-domains
17661
10
-
UDP-N-acetyl-D-glucosamine
-
-
17661
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
7
-
2-acetamido-2-deoxy-alpha-D-glucopyranosyl 1-diphosphate
-
-
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7.2
-
-
assay at
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
-
broad pH-range within enzyme is active
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-
assay at
37
-
-
assay at
LOCALIZATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
additional information
-
cell-wall membrane fraction
-
Manually annotated by BRENDA team
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20°C, 50% v/v glycerol, 5mg/ml bovine serum albumin, at least 5 months, stable
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
His-Tag affinity chromatography
-
partial, recombinant enzyme expressed in Escherichia coli
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
overexpression in Escherichia coli BL21
-
lgtA gene encoding N-acetylglucosamine glycosyltransferase is cloned and expressed in Escherichia coli DH5alphapcnB, predicted amino acid sequence
-
lgtA lipooligosaccharide N-acetylglucosamine glycosyltransferase gene, amino acid sequence
-
cloning and overexpression of lgtA gene encoding enzyme in Escherichia coli BL21(DE3)/pLys, polypeptide of 333 amino acids
-
expressed in Escherichia coli
-
rfaK gene encodes the alpha-1,2-N-acetylglucosamine transferase, 1065-bp open reading frame, rfaK gene is cotranscribed with lgtF as polycistronic message from a promoter upstream of lgtF: ice operon, lgtA gene encodes beta-1,3-N-acetylglucosamine transferase
-
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
additional information
-
isogenic mutant, strain 35000HP-RSM212, with insertionally inactivated lgtA gene lacks N-acetylglucosamine and distal sugars in the lipooligosaccharide produced by the parental strain 35000HP
additional information
-
Tn916 mutagenesis: insertion mutant with inactivated enzyme prevents addition of GlcNAc and alpha-chain lacto-N-neotetraose to the lipooligosaccharide inner core
additional information
-
Tn916 mutagenesis: insertion mutant with inactivated enzyme prevents addition of GlcNAc and alpha-chain lacto-N-neotetraose to the lipooligosaccharide inner core
-
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
synthesis
-
enzyme promise to be a useful catalyst in the preparation of both GlcNAcbeta1-3Gal and GalNAc1-3Gal linkages
synthesis
-
enzyme promise to be a useful catalyst in the preparation of both GlcNAcbeta1-3Gal and GalNAc1-3Gal linkages
-