Information on EC 2.4.1.40 - glycoprotein-fucosylgalactoside alpha-N-acetylgalactosaminyltransferase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

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EC NUMBER
COMMENTARY hide
2.4.1.40
-
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RECOMMENDED NAME
GeneOntology No.
glycoprotein-fucosylgalactoside alpha-N-acetylgalactosaminyltransferase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
UDP-N-acetyl-alpha-D-galactosamine + glycoprotein-alpha-L-fucosyl-(1->2)-D-galactose = UDP + glycoprotein-N-acetyl-alpha-D-galactosaminyl-(1->3)-[alpha-L-fucosyl-(1->2)]-D-galactose
show the reaction diagram
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
hexosyl group transfer
-
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
ABH and Lewis epitopes biosynthesis from type 1 precursor disaccharide
-
-
ABH and Lewis epitopes biosynthesis from type 2 precursor disaccharide
-
-
Glycosphingolipid biosynthesis - lacto and neolacto series
-
-
Metabolic pathways
-
-
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SYSTEMATIC NAME
IUBMB Comments
UDP-N-acetyl-D-galactosamine:glycoprotein-alpha-L-fucosyl-(1->2)-D-galactose 3-N-acetyl-D-galactosaminyltransferase
Acts on blood group substance, and can use a number of 2-fucosyl-galactosides as acceptors.
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CAS REGISTRY NUMBER
COMMENTARY hide
9067-69-0
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain ATCC 43772, gene bgtA
-
-
Manually annotated by BRENDA team
crab-eating monkey
-
-
Manually annotated by BRENDA team
Syrian hamster
-
-
Manually annotated by BRENDA team
strain BFM/2Msf, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
Uniprot
Manually annotated by BRENDA team
strain BFM/2Msf, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
Uniprot
Manually annotated by BRENDA team
strain CAST/Ei and HMI/Msf, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
Uniprot
Manually annotated by BRENDA team
strain CAST/Ei and HMI/Msf, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
Uniprot
Manually annotated by BRENDA team
strain BALB/c, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
Uniprot
Manually annotated by BRENDA team
strain BALB/c, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
Uniprot
Manually annotated by BRENDA team
strain ZBN, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
-
-
Manually annotated by BRENDA team
strain ZBN, has a cis-AB gene that encodes an enzyme with both A and B transferase activities
-
-
Manually annotated by BRENDA team
chimpazee
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-N-acetyl-alpha-D-galactosamine + 2'-fucosyllactose
UDP + N-acetyl-alpha-D-galactosaminyl-(1,3)-[2'-fucosyllactose]
show the reaction diagram
-
-
-
?
UDP-N-acetyl-D-galactosamine + 2'-fucosyllactose
UDP + N-acetyl-alpha-D-galactosaminyl-2'-fucosyllactose
show the reaction diagram
UDP-N-acetyl-D-galactosamine + alpha-L-fucosyl-1-2-D-galactosyl-O-R
UDP + N-acetyl-alpha-D-galactosaminyl-1,3-[alpha-L-fucosyl-1-2]-D-galactosyl-O-R
show the reaction diagram
UDP-N-acetyl-D-galactosamine + alpha-L-Fucp-(1,2)-beta-D-Galp-(1,3)-beta-DGlcNAcp-O(CH2)7CH3
?
show the reaction diagram
-
41% of the activity with alpha-L-Fucp-(1,2)-beta-D-Galp-O(CH2)7CH3
-
-
?
UDP-N-acetyl-D-galactosamine + alpha-L-Fucp-(1,2)-beta-D-Galp-(1,4)-beta-D-GlcNAcp-O-(CH2)8CO2CH3
?
show the reaction diagram
-
79% of the activity with alpha-L-Fucp-(1,2)-beta-D-Galp-O(CH2)7CH3
-
-
?
UDP-N-acetyl-D-galactosamine + alpha-L-Fucp-(1,2)-beta-D-Galp-O(CH2)7CH3
UDP + alpha-D-GalNAc-(1,3)-[alpha-(Fucp-(1,2)])-beta-D-Galp-O(CH2)7CH3
show the reaction diagram
-
-
-
-
?
UDP-N-acetyl-D-galactosamine + asialo-porcine submaxillary mucin of A-negative blood-type
UDP + N-acetyl-alpha-D-galactosaminyl-1,3-[asialo-porcine submaxillary mucin of A-negative blood-type]
show the reaction diagram
-
-
-
-
?
UDP-N-acetyl-D-galactosamine + glycoprotein alpha-L-fucosyl-1,2-D-galactose
UDP + glycoprotein N-acetyl-alpha-D-galactosaminyl-1,3-[alpha-L-fucosyl-1,2]-D-galactose
show the reaction diagram
UDP-N-acetyl-D-galactosamine + glycoprotein-alpha-L-fucosyl-(1,2)-D-galactose
UDP + glycoprotein-N-acetyl-alpha-D-galactosaminyl-(1,3)-[alpha-L-fucosyl-(1,2)]-D-galactose
show the reaction diagram
UDP-N-acetyl-D-galactosamine + L-fucosyl-alpha-1,2-beta-galactosyl-O(CH2)7CH3
UDP + alpha-D-galactosaminyl-1,3-[alpha-L-fucosyl-1,2]-beta-D-galactosyl-O(CH2)7CH3
show the reaction diagram
UDP-N-acetyl-D-galactosamine + lacto-N-fucopentaose I
UDP + N-acetyl-alpha-D-galactosaminyl-1,3-[lacto-N-fucopentaose I]
show the reaction diagram
-
i.e. Fucalpha(1-2)Galbeta(1-3)GlcNAcbeta(1-3)Galbeta(1-4)Glc
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-
-
UDP-N-acetyl-D-galactose + 2'-fucosyllactose
UDP + N-acetyl-D-galactosyl-1-3-2'-fucosyllactose
show the reaction diagram
-
-
-
?
UDP-N-acetyl-D-galactose + H type 3-Sp-biotin
UDP + ?
show the reaction diagram
H type 3-Sp-biotin is the preferred substrate
-
-
?
UDP-N-acetyl-D-glucosamine + L-fucosyl-alpha-1,2-beta-glucosyl-O(CH2)7CH3
UDP + N-acetyl-alpha-D-glucosaminyl-1,3-[alpha-L-fucosyl-1,2]-beta-D-glucosyl-O(CH2)7CH3
show the reaction diagram
UDP-N-acetylgalactosamine + octyl 3-O-methyl-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
UDP + N-acetyl-alpha-D-galactosamine-1,3-[3-O-methyl-alpha-L-fucosyl-1,2]-beta-D-galactosyl-O(CH2)7CH3
show the reaction diagram
-
-
-
-
?
UDP-N-acetylgalactosamine + octyl 4-O-methyl-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
UDP + N-acetyl-alpha-D-galactosaminyl-1,3-[4-O-methyl-alpha-L-fucosyl-1,2]-beta-D-galactosyl-O(CH2)7CH3
show the reaction diagram
-
-
-
-
?
UDP-N-acetylgalactosamine + octyl alpha-L-xylo-hexopyranosyl-(1-2)-beta-D-galactopyranoside
UDP + N-acetyl-alpha-D-galactosaminyl-1,3-[alpha-L-xylo-hexopyranosyl-1,2]-beta-D-galactosyl-O(CH2)7CH3
show the reaction diagram
-
-
-
-
?
UDP-N-acetylgalactosamine + octyl beta-D-arabinopyranosyl-(1-2)-beta-D-galactopyranoside
UDP + N-acetyl-alpha-D-galactosaminyl-1,3-[beta-D-arabinopyranosyl-1,2-beta-D-galactosyl-O(CH2)7CH3]
show the reaction diagram
-
-
-
-
?
additional information
?
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
UDP-N-acetyl-D-galactosamine + alpha-L-fucosyl-1-2-D-galactosyl-O-R
UDP + N-acetyl-alpha-D-galactosaminyl-1,3-[alpha-L-fucosyl-1-2]-D-galactosyl-O-R
show the reaction diagram
-
H-antigen disaccharide
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-
-
UDP-N-acetyl-D-galactosamine + glycoprotein-alpha-L-fucosyl-(1,2)-D-galactose
UDP + glycoprotein-N-acetyl-alpha-D-galactosaminyl-(1,3)-[alpha-L-fucosyl-(1,2)]-D-galactose
show the reaction diagram
additional information
?
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2'-fucosyllactose
-
substrate inhibition above 1 mM
alpha-L-fucosyl-1-2-beta-D-(3-amino)-galactosyl-O-R
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complex mode inhibitor, binding structure, Leu226 is involved by interacting with the C3-position group
alpha-L-fucosyl-1-2-beta-D-(3-deoxy)-galactosyl-O-R
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competitive inhibitor, binding structure, Leu226 is involved by interacting with the C3-position group
Fluorescein mercuriacetate
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-
GDP
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weak
lacto-N-fucopentaose I
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substrate inhibition above 2 mM
N-ethylmaleimide
-
weak
octyl 3'-amino-3'-deoxy-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
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98% inhibition at 0.025 mM
octyl 3-O-methyl-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
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-
octyl alpha-L-fucopyranosyl-(1-2)-beta-D-gulopyranoside
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36% inhibition at 0.025 mM
UDP-galactose
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-
uridine
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-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.27 - 0.47
2'-fucosyllactose
1.3
alpha-L-Fucp-(1,2)-beta-D-Galp-(1,3)-beta-DGlcNAcp-O(CH2)7CH3
-
37°C, pH 7.0
0.49
alpha-L-Fucp-(1,2)-beta-D-Galp-(1,4)-beta-D-GlcNAcp-O-(CH2)8CO2CH3
-
37°C, pH 7.0
0.087
alpha-L-Fucp-(1,2)-beta-D-Galp-O(CH2)7CH3
-
37°C, pH 7.0
0.0087 - 0.167
L-fucosyl-alpha-1,2-beta-galactosyl-O(CH2)7CH3
0.35
lacto-N-fucopentaose I
-
-
0.02
octyl 3-O-methyl-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
-
-
1.14
octyl 4-O-methyl-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
-
-
0.208
octyl beta-D-arabinopyranosyl-(1-2)-beta-D-galactopyranoside
-
-
0.0099 - 3.74
UDP-GalNAc
0.242
UDP-GlcNAc
-
additional information
additional information
-
kinetics of recombinant wild-type GTA 53-354 and of GTA/GTB mutant chimeric enzymes
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.3
alpha-L-Fucp-(1,2)-beta-D-Galp-(1,3)-beta-DGlcNAcp-O(CH2)7CH3
Homo sapiens
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37°C, pH 7.0
1.8
alpha-L-Fucp-(1,2)-beta-D-Galp-(1,4)-beta-D-GlcNAcp-O-(CH2)8CO2CH3
Homo sapiens
-
37°C, pH 7.0
7.6
alpha-L-Fucp-(1,2)-beta-D-Galp-O(CH2)7CH3
Homo sapiens
-
37°C, pH 7.0
0.000333
UDP-Gal
Homo sapiens
-
-
0.0817 - 0.292
UDP-GalNAc
0.00035
UDP-GlcNAc
Homo sapiens
-
-
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0002
octyl 3'-amino-3'-deoxy-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
-
-
1
octyl 3-O-methyl-alpha-L-fucopyranosyl-(1-2)-beta-D-galactopyranoside
-
-
0.022
octyl alpha-L-fucopyranosyl-(1-2)-beta-D-gulopyranoside
-
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.2
-
plasma
5.7
-
lung
additional information
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-
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6
-
assay at
6.4
-
blood group A1
6.5 - 7
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-
7 - 7.4
-
-
7
-
pancreatic cancer cell line, antrum and distal colon
7.6
-
blood group A2
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
A-type enzyme expression
Manually annotated by BRENDA team
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middle and distal
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
A-type enzyme expression
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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PDB
SCOP
CATH
ORGANISM
UNIPROT
Bacteroides ovatus (strain ATCC 8483 / DSM 1896 / JCM 5824 / NCTC 11153)
Bacteroides ovatus (strain ATCC 8483 / DSM 1896 / JCM 5824 / NCTC 11153)
Bacteroides ovatus (strain ATCC 8483 / DSM 1896 / JCM 5824 / NCTC 11153)
Bacteroides ovatus (strain ATCC 8483 / DSM 1896 / JCM 5824 / NCTC 11153)
Bacteroides ovatus (strain ATCC 8483 / DSM 1896 / JCM 5824 / NCTC 11153)
Escherichia coli (strain K12)
Escherichia coli (strain K12)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35000
-
x * 35000, SDS-PAGE with and without 2-mercaptoethanol
40000
-
x * 40000, SDS-PAGE
46000
-
2 * 46000, sedimentation equilibrium of reduced and carboxymethylated enzyme
52000
-
2 * 52000, SDS-PAGE of carboxymaleyl enzyme
90000 - 100000
-
gel filtration
100000
-
zonal centrifugation, gel filtration
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
structure analysis of GTA/GTB chimeric enzymes GTB/G176R and GTB/G176R/G235S bound to a panel of donor and acceptor analogue substrates, open, semi-closed, and closed conformations, overview
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POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
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Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a large single crystal is subjected to H/D exchange prior to data collection and time-of-flight neutron diffraction data is collected to 2.5 A resolution at the Protein Crystallography Station to 85% overall completeness, with complementary X-ray diffraction data collected from a crystal from the same drop and extending to 1.85 A resolution
-
crystals of purified native enzyme are soaked with various combinations of UDP-GalNAc, UDP-Gal, UDP, and acceptor analogues alpha-L-fucosyl-1-2-beta-D-(3-deoxy)-galactosyl-O-R or alpha-L-fucosyl-1-2-beta-D-(3-amino)-galactosyl-O-R, ligands are solved in 7.5% PEG 4000, 15% glycerol, 75 mM N-[2-acetamido]-2-iminodiacetic acid, pH 7.5, 10 mM MnCl2, and 10 mM inhibitor, 3-4 days, X-ray diffraction structure determination and analysis at 2.1 A resolution
-
enzyme soaked with acceptor analogs: galactose, lactose, N-acetyllactosamine, beta-D-Galp-O(CH2)8CO2CH3, alpha-L-Fucp-(1,2)-beta-D-Galp-O(CH2)7CH3, beta-D-Galp-(1,4)-beta-D-Glcp-OCH3, alpha-L-Fucp-(1,2)-beta-D-Galp-(1,3)-beta-D-GlcNAcp-O(CH2)7CH3, alpha-L-Fucp-(1,2)-beta-D-Galp-(1,4)-beta-D-GlcNAcp-O-(CH2)8CO2CH3
-
G176R/P234S/S235G/M266L/A268G-mutant with and without H-antigen, at 1.55 and 1.65 A resolution respectively; of catalytic domain residues 63-354, with and without L-fucosyl-alpha-1,2-beta-galactosyl-O(CH2)7CH3-acceptor and UDP, at 1.35 and 1.8 A resolution respectively
purified recombinant GTA/GTB mutant chimeric enzymes, complexing with synthetic antigen disaccharides or UDP, hanging drop vapour diffusion method, different solutions for the different chimeric mutants, X-ray diffraction structure determinationand analysis at 1.41-1.75 A resolution, overview, structure modelling
-
structures of GTA, GTB and several chimeras determined by single-crystal X-ray diffraction demonstrate a range of susceptibility to the choice of cryoprotectant, in which the mobile polypeptide loops can be induced by glycerol to form the ordered closed conformation associated with substrate recognition and by MPD (hexylene glycol, 2-methyl-2,4-pentanediol) to hinder binding of substrate in the active site owing to chelation of the Mn2+ cofactor and thereby adopt the disordered open state
-
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TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
30 min, 5% loss of activity
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
enzyme is not stable in crude plasma
-
irreversible inactivation in absence of Triton X-100
-
loss of activity after freezing in buffer of pH 7.5
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, rapid loss of activity
-
-60°C, 2 mM MnCl2, 1 mM EDTA, 0.02 mM UDP, stable for up to 30 days
-
-70°C, 0.025 M MES buffer, pH 6.0, 1 mM EDTA, 0.03% Triton X-100, after removal of most of the buffer by dialysis, stable for 1 year
-
-80°C, 20% loss of activity after 1 year
-
4°C, 0.05 M Tris-HCl, pH 7.4, 2 mM MnCl2, 1 mM EDTA, 0.01% w/v Triton X-100, 0.2 M NaCl, 1 mM dithiothreitol, 0.03% w/v NaN3, 10% loss of activity per month
-
4°C, 25% loss of activity after storage of plasma for 2 weeks
-
4°C, pH 7.5, half-life is about 3 months
-
4°C, rapid loss of activity of purified enzyme
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
blood group A
-
blood group A; partial
-
recombinant wild-type GTA 53-354 and of GTA/GTB mutant chimeric enzymes from Escherichia coli
-
using a two-step protocol consisting of ion-exchange chromatography followed by UDP-hexanolamine affinity chromatography
-
via ELISA
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
A-type Abo gene A1, DNA and amino acid sequence determination and analysis, functional expression in CHO cells expressing the H precursor; A-type Abo gene A2, DNA and amino acid sequence determination and analysis, functional expression in CHO cells expressing the H precursor; A-type Abo gene A4, DNA and amino acid sequence determination and analysis; A-type gene Abo A3, DNA and amino acid sequence determination and analysis
expressed in chinese hamster ovary carcinoma cells, already stable transfected with an alpha1,2-fucosyltransferase
-
expressed in Escherichia coli
-
expressed in Escherichia coli BL21, P234S-mutant of blood-group substance B-dependent galactosyltransferase
expressed in Escherichia coli TG-1
-
expression of truncated wild-type GTA 53-354 and of GTA/GTB mutant chimeric enzymes in Escherichia coli
-
human GTA with the N-terminal transmembrane domain truncated at residue Met63 and codon-optimized for BL21 Escherichia coli is expressed and purified from cultures using a two-step protocol consisting of ion-exchange chromatography followed by UDP-hexanolamine affinity chromatography
-
transfected into HeLa cells derived from human adenocarcinoma of uterus
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G176R/P234S/S235G/M266L/A268G
expressed in Escherichia coli BL21, although 4 of the mutations correspond to a change from A- to B-blood group, the P234S-mutation shows a remarkable increase in A-donor specificity
additional information
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
-
the enzyme possesses flexible substrate specificity and can therefore be used to synthesize five different types of A antigens with high efficiency, engineering of bacterial cell surface polysaccharides by BgtA, overview
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LINKS TO OTHER DATABASES (specific for EC-Number 2.4.1.40)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)