2.4.1.133: xylosylprotein 4-beta-galactosyltransferase
This is an abbreviated version!
For detailed information about xylosylprotein 4-beta-galactosyltransferase, go to the full flat file.
Word Map on EC 2.4.1.133
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2.4.1.133
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proteoglycans
-
glycosaminoglycans
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ehlers-danlos
-
beta-1,4-galts
-
progeroid
-
xylosyltransferase
-
larsen
-
hypermobility
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b3galt6
-
laxity
-
hypermobl
-
reunion
-
linkeropathies
-
spondylodysplastic
-
hyperextensibility
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drug development
- 2.4.1.133
- proteoglycans
- glycosaminoglycans
- ehlers-danlos
- beta-1,4-galts
-
progeroid
-
xylosyltransferase
-
larsen
- hypermobility
- b3galt6
- laxity
-
hypermobl
-
reunion
-
linkeropathies
-
spondylodysplastic
-
hyperextensibility
- drug development
Reaction
Synonyms
B4GALT7, beta-1,4 galactosyltransferase I, beta-1,4 galactosyltransferase V, beta-1,4-galactosyltransferase, beta-1,4-galactosyltransferase 7, beta-1,4-galactosyltransferase I, beta-1,4-galactosyltransferase-I, beta-1,4-galactosyltransferase-T7, beta-1,4-GalT, beta-1,4-GalT 7, beta-1,4-GalT I, beta-1,4-GalT V, beta-1,4-GalT-I, beta1,4-galactosyltransferase 7, beta1,4-galactosyltransferase I, beta1,4-galactosyltransferase VII, beta1,4-galactosyltransferase-7, beta1,4-GalT, beta1,4-GalT-I, beta1,4-GalT7, beta4-galactosyltransferase 7, beta4Gal-T7, beta4galactosyltransferase I, beta4GalT-7, beta4GalT7, dbeta4GalTI, galactosyltransferase I, galactosyltransferase, uridine diphosphogalactose-xylose, GalT I, GalT-I, hbeta4GalT7, MgGalT7, pNP-xylose-beta-1,4-galactosyltransferase, proteoglycan UDP-galactose:beta-xylose beta 1,4-galactosyltransferase I, SQV-3, UDP-D-galactose:D-xylose galactosyltransferase, UDP-D-galactose:xylose galactosyltransferase, UDP-galactose:O-beta-D-xylosylprotein 4-beta-D-galactosyltransferase, UDPgalactose:O-beta-D-xylosylprotein 4-beta-D-galactosyltransferase, xylosylprotein 4-beta-galactosyltransferase, xylosylprotein beta1,4-galactosyltransferase
ECTree
2.4.1.133 xylosylprotein 4-beta-galactosyltransferaseAdvanced search results
results (
results (Substrates Products
Substrates Products on EC 2.4.1.133 - xylosylprotein 4-beta-galactosyltransferase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
4-nitrophenyl beta-D-xylopyranoside + UDP-alpha-D-galactose
UDP + 4-nitrophenyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
-
-
-
?
UDP-alpha-D-galactose + (1R,2S,3R,4R)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol
UDP + ?
-
-
-
?
UDP-alpha-D-galactose + (1S,2R,3S,4S)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol
UDP + ?
-
-
-
?
UDP-alpha-D-galactose + 2-naphthyl 1,5-dithio-beta-D-xylopyranoside
UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-1,5-dithio-beta-D-xylopyranoside
-
-
-
?
UDP-alpha-D-galactose + 2-naphthyl 5-thio-beta-D-xylopyranoside
UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside
-
-
-
?
UDP-alpha-D-galactose + 2-naphthyl beta-D-xylopyranoside
UDP + 4-beta-D-galactosyl-2-naphthyl-beta-D-xylopyranoside
-
-
-
?
UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-D-carbaxylopyranoside
UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-D-carbaxylopyranoside
a 5a-carba-beta-xylopyranoside
-
-
?
UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-L-carbaxylopyranoside
UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-L-carbaxylopyranoside
a 5a-carba-beta-xylopyranoside
-
-
?
UDP-alpha-D-galactose + 4-methylumbelliferyl alpha-D-xylopyranoside
UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
-
-
?
UDP-alpha-D-galactose + 4-methylumbelliferyl beta-D-xylopyranoside
UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
-
-
-
?
UDP-alpha-D-galactose + 4-methylumbelliferyl-beta-D-xylopyranoside
UDP + ?
the strategic position of Tyr194 forming stacking interactions with the aglycone, and the hydrogen bond between the His195 nitrogen backbone and the carbonyl group of the coumarinyl molecule to develop a tight binder of the enzyme. This leads to the synthesis of 4-deoxy-4-fluoroxylose linked to 4-methylumbelliferone that inhibits enzyme activity in vitro with a Ki 10 times lower than the Km value and efficiently impairs glycosaminoglycan synthesis in a cell assay. Molecular modeling of the enzyme's active site in the presence of UDP-alpha-D-galactose and 4-methylumbelliferyl-beta-D-xylopyranoside using the crystal structure of Drosophila melanogaster enzyme dbeta4GalT7, PDB code 4M4K, overview
-
-
?
UDP-alpha-D-galactose + beciparcil
UDP + 4-[(4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranosyl)thio]benzonitrile
a 5-thio-beta-D-xylopyranoside
-
-
?
UDP-alpha-D-galactose + iliparcil
UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside
a 5-thio-beta-D-xylopyranoside
-
-
?
UDP-alpha-D-galactose + naphthalen-2-yl 1-thio-beta-D-xylopyranoside
UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-1-thio-beta-D-xylopyranoside
-
-
-
?
UDP-alpha-D-galactose + naphthalen-2-yl beta-D-xylopyranoside
UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
-
-
?
UDP-alpha-D-galactose + naroparcil
UDP + 4-[4-[(4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranosyl)thio]benzoyl]benzonitrile
a 5-thio-beta-D-xylopyranoside
-
-
?
UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein]
UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]
UDP-alpha-D-galactose + odiparcil
UDP + 4-methyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside
a 5-thio-beta-D-xylopyranoside
-
-
?
UDP-galactose + 4-methylumbelliferyl O-beta-D-xylopyranoside
UDP + 4-methylumbelliferyl 4-O-beta-D-galacto-pyranosyl-beta-D-xylopyranoside
-
-
-
-
?
UDP-galactose + 4-methylumbelliferyl O-beta-D-xylopyranoside
UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
-
-
?
UDP-galactose + 4-methylumbelliferyl O-beta-D-xylopyranoside
UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranoyl-beta-D-xylopyranoside
-
-
-
-
?
UDP-galactose + 4-nitrophenyl O-beta-D-xylopyranoside
UDP + 4-nitrophenyl 4-O-beta-D-galacto-pyranosyl-beta-D-xylopyranoside
-
-
-
-
?
UDP-galactose + 4-nitrophenyl O-beta-D-xylopyranoside
UDP + 4-nitrophenyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
UDP-galactose + N-[O-(beta-D-xylopyranosyl)-3-hydroxypropyl]phthalamate
?
-
-
-
-
?
UDP-galactose + N-[O-(beta-D-xylopyranosyl)-3-hydroxypropyl]succinamate
?
-
-
-
-
?
UDP-galactose + O-gamma-2,3,4-tri-O-acetyl-(beta-D-xylopyranosyl)-N-Cbz-L-serine methyl ester
?
-
-
-
-
?
UDP-galactose + O-gamma-beta-D-xylopyranosyl-N-Cbz-L-serine methyl ester
?
-
-
-
-
?
UDP-galactose + p-nitrophenyl-beta-D-xyloside
UDP + Galbeta(1-4)Xylbeta-p-nitrophenyl
-
-
-
-
?
UDP-glucuronic acid + 4-methylumbelliferyl-beta-D-xylopyranoside
?
-
-
-
?
UDP-N-acetyl glucosamine + 4-methylumbelliferyl-beta-D-xylopyranoside
?
-
-
-
?
UDPgalactose + 4-methylumbelliferyl-beta-D-xyloside
UDP + beta-D-galactosyl-1,4-beta-D-xylosyl-1-O-(4-methylumbelliferone)
UDPgalactose + beta-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,6-(N-acetyl-beta-D-glucosaminyl-1,2)-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
UDP + beta-D-galactosyl-1,4-beta-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,6-(N-acetyl-beta-D-glucosaminyl-1,2)-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
-
-
-
-
?
UDPgalactose + N-acetyl-beta-D-glucosamine
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
UDPgalactose + N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
-
-
-
-
?
UDPgalactose + N-acetyl-beta-D-glucosaminyl-1,6-(beta-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,2)-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,6-(beta-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,2)-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
-
-
-
-
?
UDPgalactose + N-acetyl-beta-D-glucosaminyl-1,6-(N-acetyl-beta-D-glucosaminyl-1,2)-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,6-(N-acetyl-beta-D-glucosaminyl-1,2)-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
-
-
-
-
?
UDPgalactose + N-acetyl-beta-D-glucosaminyl-1,6-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,6-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl
-
-
-
-
?
UDPgalactose + p-nitrophenyl beta-D-xylopyranoside
UDP + beta-D-galactopyranosyl-1,4-xylopyranosyl-1-O-nitrophenol
UDPgalactose + p-nitrophenyl beta-D-xylose
UDP + beta-D-galactosyl-1,4-beta-D-xylosyl-1-O-nitrophenol
-
-
-
-
?
UDPgalactose + p-nitrophenyl N-acetyl-beta-D-glucosaminide
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminide-1-O-nitrophenol
-
-
-
-
?
UDPgalactose + xylosylserine
UDP + beta-D-galactosyl-1,4-beta-D-xylosylserine
-
-
-
-
?
UDP-alpha-D-galactose + D-xylose
UDP + 4-O-beta-D-galactosyl-beta-D-xylose
-
-
-
?
UDP-alpha-D-galactose + D-xylose
UDP + 4-O-beta-D-galactosyl-beta-D-xylose
-
-
-
?
UDP-alpha-D-galactose + D-xylose
UDP + 4-O-beta-D-galactosyl-beta-D-xylose
-
-
-
?
UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein]
UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]
-
-
-
?
UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein]
UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]
-
-
-
?
UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein]
UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein]
-
-
-
?
UDP-galactose + 4-nitrophenyl O-beta-D-xylopyranoside
UDP + 4-nitrophenyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
-
-
-
?
UDP-galactose + 4-nitrophenyl O-beta-D-xylopyranoside
UDP + 4-nitrophenyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside
-
-
-
?
UDP-galactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
-
-
?
UDP-galactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
the enzyme transfers a galactose to the beta-xylose residue in proteolycan
-
-
?
UDP-galactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
-
-
-
?
UDP-galactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
-
-
?
UDP-galactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
the enzyme is unable to catalyze the transfer of galactose from UDP-galactose onto xylose when this residue is phosphorylated at the C-2 position
-
-
?
UDP-galactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
in a progeroid patient carrying two point mutations in beta4galactosyltransferase I (ß4GalT-7) only 50% of the decorin core protein molecules are substituted with glycosaminoglycan chains. Tthe ß4GalT-7 mutations directly affect the molecular phenotype of decorin observed in a patient with the progeroid form of Ehlers-Danlos syndrome, which may be a major mechanistic cause for the skin and wound healing defects observed in this patient
-
-
?
UDP-galactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
-
-
-
?
UDPgalactose + 4-methylumbelliferyl-beta-D-xyloside
UDP + beta-D-galactosyl-1,4-beta-D-xylosyl-1-O-(4-methylumbelliferone)
-
-
-
-
?
UDPgalactose + 4-methylumbelliferyl-beta-D-xyloside
UDP + beta-D-galactosyl-1,4-beta-D-xylosyl-1-O-(4-methylumbelliferone)
-
assay method for measuring the galactosyltransferase I activity with D-galactal as inhibitor for endogenous beta-galactosidase
-
-
?
UDPgalactose + N-acetyl-beta-D-glucosamine
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
-
-
-
-
?
UDPgalactose + N-acetyl-beta-D-glucosamine
UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine
-
-
or poly-beta4-N-acetyllactosamine structures in glycoconjugates
?
UDPgalactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
the enzyme transfers a galactose to the beta-xylose residue in proteolycan. The enzyme is essential for viability
-
-
?
UDPgalactose + O-beta-D-xylosylprotein
UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein
-
involved in chondroitin sulfate biosynthesis
-
-
?
UDPgalactose + p-nitrophenyl beta-D-xylopyranoside
UDP + beta-D-galactopyranosyl-1,4-xylopyranosyl-1-O-nitrophenol
-
-
-
-
?
UDPgalactose + p-nitrophenyl beta-D-xylopyranoside
UDP + beta-D-galactopyranosyl-1,4-xylopyranosyl-1-O-nitrophenol
-
-
-
-
?
additional information
?
-
enzymatic galactosylation reaction using epimerase UDP-glucose 4-epimerase MgUGE (EC 5.1.3.2) and beta-1,4-galactosyltransferase MgGalT7 with 4-nitrophenol xylose and UDP-glucose as substrates, mass spectrometric analyses of the acceptor substrate and the galactosylated reaction product, coupled assay method, evaluation, overview
-
-
-
additional information
?
-
donor and acceptor substrate binding, structure analysis, overview
-
-
?
additional information
?
-
beta-1,4-galactosyltransferase is responsible for the biosynthesis of Gal-beta - 4GlcNAc units in N-glycans and core 2 O-glycans of glycoproteins, including IgG, gp120 and serum alpha-fetoprotein
-
-
?
additional information
?
-
enzyme is able to transfer glucose, xylose and, to a lesser extent glucuronic acid and N-acetylglucosamine, to acceptor sugars, whereas UDP-mannose and UDP-N-acetyl galactosamine are not substrates
-
-
?
additional information
?
-
-
enzyme is able to transfer glucose, xylose and, to a lesser extent glucuronic acid and N-acetylglucosamine, to acceptor sugars, whereas UDP-mannose and UDP-N-acetyl galactosamine are not substrates
-
-
?
additional information
?
-
some beta-D-xylosides, such as 2-naphthyl beta-D-xylopyranoside, can induce glycosaminoglycan synthesis by serving as acceptor substrates for beta4GalT7 and by that also compete with the glycosaminoglycan synthesis on core proteins
-
-
?
additional information
?
-
donor and acceptor substrate binding, strutcure analysis, overview
-
-
?
additional information
?
-
structure-activity relationships for beta4GalT7 and xylosides with modifications of the aromatic aglycon, using enzymatic assays, cell studies, and molecular docking simulations, show that the aglycons reside on the outside of the active site of the enzyme and that quite bulky aglycons are accepted. Increased galactosylation with increased linker length is observed, substrate specificity with glycosides, detailed overview. The galactosylation is influenced by the identity and position of substituents in the aromatic framework, and generally, only xylosides with beta-glycosidic linkages function as good substrates for the enzyme. The galactosylation ability of a xyloside is increased by replacing the anomeric oxygen with sulfur, but decreased by replacing it with carbon. Enzyme reaction kinetics of galactosylation are dependent on subtle differences in orientation of the xylose moiety
-
-
?
additional information
?
-
the enzyme catalyzes the transfer of galactose from uridine diphosphogalactose to terminal N-acetylglucosamine, forming the Galbeta1-4GlcNAc structure
-
-
?
additional information
?
-
synthesis of xyloside analogues with substitution of the endocyclic oxygen atom by sulfur or carbon and investigation of them as substrates for beta-1,4-galactosyltransferase 7 (beta4GalT7), overview. The analogues with an endocyclic sulfur atom prove to be excellent substrates for b4GalT7, and are galactosylated approx. fifteen times more efficiently than the corresponding xyloside. The 5a-carba-beta-xylopyranoside in the D-configuration proves to be a good substrate for beta4GalT7, whereas the enantiomer in the L-configuration shows no activity. X-ray crystallography, NMR spectroscopy, and molecular modeling provide a rationale for the pronounced activity of the sulfur analogues. Favorable Pi-Pi interactions between the 2-naphthyl moiety and a tyrosine side chain of the enzyme are observed for the thio analogues (1S,2R,3S,4S)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol, 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one, and 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one. The carbaxyloside of iliparcil are synthesized as well as its L-xylo-enantiomers 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one and 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one. The L-xylo-derivative 4-ethyl-6-([(1S,2S,3R,4S)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one shows a much higher antithrombotic activity compared to the D-xylo-enantiomer 4-ethyl-6-([(1R,2R,3S,4R)-2,3,4-trihydroxycyclohexyl]oxy)-2H-1-benzopyran-2-one and only the compound with L-xylo conformation functions as substrate for beta4GalT7 when assayed with enzyme extracts from chicken embryo. This is in stark contrast to other investigations where L-enantiomers of xylosides rarely act as substrates for beta4GalT7. Quantum mechanical calculations and docking simulations, overview
-
-
-
additional information
?
-
-
enzyme catalyzes the transfer of galactose from the sugar nucleotide donor uridine diphosphate galactose to glycoside residues with a terminal N-acetylglucosamine moiety
-
-
?
additional information
?
-
-
enzyme transfers galactose to the terminal N-acetylglucosamine of N- and O-linked glycans in a beta-1,4-linkage
-
-
?
