2.4.1.133 4-nitrophenyl beta-D-xylopyranoside + UDP-alpha-D-galactose - Homo sapiens UDP + 4-nitrophenyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside - ? 420090 2.4.1.133 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 Homo sapiens ? - ? 89 2.4.1.133 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 Rattus norvegicus ? - ? 89 2.4.1.133 additional information enzyme transfers galactose to the terminal N-acetylglucosamine of N- and O-linked glycans in a beta-1,4-linkage Rattus norvegicus ? - ? 89 2.4.1.133 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 Homo sapiens ? - ? 89 2.4.1.133 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 Homo sapiens ? - ? 89 2.4.1.133 additional information donor and acceptor substrate binding, structure analysis, overview Drosophila melanogaster ? - ? 89 2.4.1.133 additional information donor and acceptor substrate binding, strutcure analysis, overview Homo sapiens ? - ? 89 2.4.1.133 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 Homo sapiens ? - ? 89 2.4.1.133 additional information the enzyme catalyzes the transfer of galactose from uridine diphosphogalactose to terminal N-acetylglucosamine, forming the Galbeta1-4GlcNAc structure Homo sapiens ? - ? 89 2.4.1.133 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 Crassostrea gigas ? - - 89 2.4.1.133 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 Homo sapiens ? - - 89 2.4.1.133 UDP-alpha-D-galactose + (1R,2S,3R,4R)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol - Homo sapiens UDP + ? - ? 458255 2.4.1.133 UDP-alpha-D-galactose + (1S,2R,3S,4S)-4-(2-naphthyloxy)cyclohexan-1,2,3-triol - Homo sapiens UDP + ? - ? 458256 2.4.1.133 UDP-alpha-D-galactose + 2-naphthyl 1,5-dithio-beta-D-xylopyranoside - Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-1,5-dithio-beta-D-xylopyranoside - ? 458257 2.4.1.133 UDP-alpha-D-galactose + 2-naphthyl 5-thio-beta-D-xylopyranoside - Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside - ? 458258 2.4.1.133 UDP-alpha-D-galactose + 2-naphthyl beta-D-xylopyranoside - Homo sapiens UDP + 4-beta-D-galactosyl-2-naphthyl-beta-D-xylopyranoside - ? 434823 2.4.1.133 UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-D-carbaxylopyranoside a 5a-carba-beta-xylopyranoside Homo sapiens UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-D-carbaxylopyranoside - ? 458259 2.4.1.133 UDP-alpha-D-galactose + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl beta-L-carbaxylopyranoside a 5a-carba-beta-xylopyranoside Homo sapiens UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-beta-L-carbaxylopyranoside - ? 458260 2.4.1.133 UDP-alpha-D-galactose + 4-methylumbelliferyl alpha-D-xylopyranoside - Homo sapiens UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside - ? 435906 2.4.1.133 UDP-alpha-D-galactose + 4-methylumbelliferyl beta-D-xylopyranoside - Homo sapiens UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside - ? 420064 2.4.1.133 UDP-alpha-D-galactose + 4-methylumbelliferyl-beta-D-xylopyranoside 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 Homo sapiens UDP + ? - ? 435909 2.4.1.133 UDP-alpha-D-galactose + beciparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-[(4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranosyl)thio]benzonitrile - ? 458261 2.4.1.133 UDP-alpha-D-galactose + D-xylose - Gallus gallus UDP + 4-O-beta-D-galactosyl-beta-D-xylose - ? 354143 2.4.1.133 UDP-alpha-D-galactose + iliparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-ethyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside - ? 458263 2.4.1.133 UDP-alpha-D-galactose + naphthalen-2-yl 1-thio-beta-D-xylopyranoside - Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-1-thio-beta-D-xylopyranoside - ? 458265 2.4.1.133 UDP-alpha-D-galactose + naphthalen-2-yl beta-D-xylopyranoside - Homo sapiens UDP + naphthalen-2-yl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside - ? 458266 2.4.1.133 UDP-alpha-D-galactose + naroparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-[4-[(4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranosyl)thio]benzoyl]benzonitrile - ? 458267 2.4.1.133 UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein] - Homo sapiens UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein] - ? 434831 2.4.1.133 UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein] - Drosophila melanogaster UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein] - ? 434831 2.4.1.133 UDP-alpha-D-galactose + O-beta-D-xylosyl-[protein] - Crassostrea gigas UDP + 4-beta-D-galactosyl-O-beta-D-xylosyl-[protein] - ? 434831 2.4.1.133 UDP-alpha-D-galactose + odiparcil a 5-thio-beta-D-xylopyranoside Homo sapiens UDP + 4-methyl-2-oxo-2H-1-benzopyran-7-yl 4-O-beta-D-galactopyranosyl-5-thio-beta-D-xylopyranoside - ? 458269 2.4.1.133 UDP-alpha-D-galactose + xylobiose - Drosophila melanogaster UDP + ? - ? 435911 2.4.1.133 UDP-galactose + 2-(6-hydroxynaphthyl) beta-D-xylopyranoside - Homo sapiens ? - ? 424210 2.4.1.133 UDP-galactose + 3-acetamido-propyl beta-D-xylopyranoside - Homo sapiens ? - ? 424211 2.4.1.133 UDP-galactose + 3-benzamido-propyl beta-D-xylopyranoside - Homo sapiens ? - ? 424212 2.4.1.133 UDP-galactose + 3-hexanamido-propyl beta-D-xylopyranoside - Homo sapiens ? - ? 424213 2.4.1.133 UDP-galactose + 4-methylumbelliferyl O-beta-D-xylopyranoside - Homo sapiens UDP + 4-methylumbelliferyl 4-O-beta-D-galacto-pyranosyl-beta-D-xylopyranoside - ? 424214 2.4.1.133 UDP-galactose + 4-methylumbelliferyl O-beta-D-xylopyranoside - Homo sapiens UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside - ? 424215 2.4.1.133 UDP-galactose + 4-methylumbelliferyl O-beta-D-xylopyranoside - Homo sapiens UDP + 4-methylumbelliferyl 4-O-beta-D-galactopyranoyl-beta-D-xylopyranoside - ? 424216 2.4.1.133 UDP-galactose + 4-methylumbelliferyl-beta-D-xylopyranoside - Homo sapiens ? - ? 421647 2.4.1.133 UDP-galactose + 4-nitrophenyl O-beta-D-xylopyranoside - Homo sapiens UDP + 4-nitrophenyl 4-O-beta-D-galacto-pyranosyl-beta-D-xylopyranoside - ? 424217 2.4.1.133 UDP-galactose + 4-nitrophenyl O-beta-D-xylopyranoside - Homo sapiens UDP + 4-nitrophenyl 4-O-beta-D-galactopyranosyl-beta-D-xylopyranoside - ? 424218 2.4.1.133 UDP-galactose + 4-nitrophenyl-alpha-D-xyloside - Crassostrea gigas UDP + ? - ? 458298 2.4.1.133 UDP-galactose + N-[O-(beta-D-xylopyranosyl)-3-hydroxypropyl]phthalamate - Homo sapiens ? - ? 424223 2.4.1.133 UDP-galactose + N-[O-(beta-D-xylopyranosyl)-3-hydroxypropyl]succinamate - Homo sapiens ? - ? 424224 2.4.1.133 UDP-galactose + O-beta-D-xylosylprotein - Homo sapiens UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 377972 2.4.1.133 UDP-galactose + O-beta-D-xylosylprotein - Rattus norvegicus UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 377972 2.4.1.133 UDP-galactose + O-beta-D-xylosylprotein - Drosophila melanogaster UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 377972 2.4.1.133 UDP-galactose + 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 Homo sapiens UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 377972 2.4.1.133 UDP-galactose + O-beta-D-xylosylprotein the enzyme transfers a galactose to the beta-xylose residue in proteolycan Drosophila melanogaster UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 377972 2.4.1.133 UDP-galactose + 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 Homo sapiens UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 377972 2.4.1.133 UDP-galactose + O-gamma-2,3,4-tri-O-acetyl-(beta-D-xylopyranosyl)-N-Cbz-L-serine methyl ester - Homo sapiens ? - ? 424225 2.4.1.133 UDP-galactose + O-gamma-beta-D-xylopyranosyl-N-Cbz-L-serine methyl ester - Homo sapiens ? - ? 424226 2.4.1.133 UDP-galactose + p-nitrophenyl-beta-D-xyloside - Homo sapiens UDP + Galbeta(1-4)Xylbeta-p-nitrophenyl - ? 389978 2.4.1.133 UDP-glucose + 4-methylumbelliferyl-beta-D-xylopyranoside - Homo sapiens ? - ? 410558 2.4.1.133 UDP-glucuronic acid + 4-methylumbelliferyl-beta-D-xylopyranoside - Homo sapiens ? - ? 410574 2.4.1.133 UDP-N-acetyl glucosamine + 4-methylumbelliferyl-beta-D-xylopyranoside - Homo sapiens ? - ? 410590 2.4.1.133 UDP-xylose + 4-methylumbelliferyl-beta-D-xylopyranoside - Homo sapiens ? - ? 410619 2.4.1.133 UDPgalactose + 4-methylumbelliferyl-beta-D-xyloside - Homo sapiens UDP + beta-D-galactosyl-1,4-beta-D-xylosyl-1-O-(4-methylumbelliferone) - ? 354148 2.4.1.133 UDPgalactose + 4-methylumbelliferyl-beta-D-xyloside assay method for measuring the galactosyltransferase I activity with D-galactal as inhibitor for endogenous beta-galactosidase Homo sapiens UDP + beta-D-galactosyl-1,4-beta-D-xylosyl-1-O-(4-methylumbelliferone) - ? 354148 2.4.1.133 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 - Mus musculus 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 - ? 354152 2.4.1.133 UDPgalactose + N-acetyl-beta-D-glucosamine - Mus musculus UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine - ? 354154 2.4.1.133 UDPgalactose + N-acetyl-beta-D-glucosamine - Mus musculus UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosamine or poly-beta4-N-acetyllactosamine structures in glycoconjugates ? 354154 2.4.1.133 UDPgalactose + N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl - Mus musculus UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,2-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl - ? 354150 2.4.1.133 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 - Mus musculus 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 - ? 354151 2.4.1.133 UDPgalactose + N-acetyl-beta-D-glucosaminyl-1,6-(N-acetyl-beta-D-glucosaminyl-1,2)-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl - Mus musculus 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 - ? 354153 2.4.1.133 UDPgalactose + N-acetyl-beta-D-glucosaminyl-1,6-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl - Mus musculus UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminyl-1,6-alpha-D-mannosyl-1,6-beta-D-mannosyl-octyl - ? 354149 2.4.1.133 UDPgalactose + O-beta-D-xylosylprotein involved in chondroitin sulfate biosynthesis Gallus gallus UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 370428 2.4.1.133 UDPgalactose + O-beta-D-xylosylprotein the enzyme transfers a galactose to the beta-xylose residue in proteolycan. The enzyme is essential for viability Drosophila melanogaster UDP + 4-beta-D-galactosyl-O-beta-D-xylosylprotein - ? 370428 2.4.1.133 UDPgalactose + p-nitrophenyl beta-D-xylopyranoside - Drosophila melanogaster UDP + beta-D-galactopyranosyl-1,4-xylopyranosyl-1-O-nitrophenol - ? 354146 2.4.1.133 UDPgalactose + p-nitrophenyl beta-D-xylopyranoside - Homo sapiens UDP + beta-D-galactopyranosyl-1,4-xylopyranosyl-1-O-nitrophenol - ? 354146 2.4.1.133 UDPgalactose + p-nitrophenyl beta-D-xylose - Drosophila melanogaster UDP + beta-D-galactosyl-1,4-beta-D-xylosyl-1-O-nitrophenol - ? 354144 2.4.1.133 UDPgalactose + p-nitrophenyl N-acetyl-beta-D-glucosaminide - Drosophila melanogaster UDP + beta-D-galactosyl-1,4-N-acetyl-beta-D-glucosaminide-1-O-nitrophenol - ? 354147 2.4.1.133 UDPgalactose + xylosylserine - Gallus gallus UDP + beta-D-galactosyl-1,4-beta-D-xylosylserine - ? 354145