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- W1976307612 abstract "N-Acetylglucosaminyltransferase-V (GlcNAcT-V) transfers a β-linked GlcNAc residue from UDP-GlcNAc to the 6-OH group of the αMan residue in oligosaccharides terminating in the sequence β-D-GlcpNAc-(1 → 2)-α-D-Manp-(1 → 6)-β-D-Glcp-OR (5, R = (CH 2 ) 7 CH 3 ). The terminal GlcNAc moiety may be replaced by a Glc residue to produce trisaccharide 6. Two thio analogs (7, 8) of trisaccharide 6, where the oxygen atoms in the glycosidic linkages between sugar residues were replaced by sulfur, were prepared by multistep chemical synthesis that made use of the key intermediates 1,2-anhydro-3,4,6-tri-O-benzyl-α-D-glucose (10) and 1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannose (13) as donors for the glycosylations. The thio analogs (7,8) were kinetically evaluated as substrates for GlcNAcT-V and found to be acceptors with two- to three-fold increase in V max but higher K m values (7, K m = 376 μM; 8, K m = 300 μM) than their parent compound 6 (K m = 111 μM), which has the natural oxygen linkage. The thio analogs 7 and 8 could be quantitatively converted into the expected product tetrasaccharides (27, 28) by incubation with GlcNAcT-V and UDP-GlcNAc. The enzymatic results indicate that GlcNAcT-V tolerates the substitution of the natural oxygen linkage of the acceptor by a sulfur linkage. Keywords: N-acetylglucosaminyltransferase-V, enzyme acceptors, trisaccharide analogs, thioglycosides." @default.
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- W1976307612 date "1997-06-01" @default.
- W1976307612 modified "2023-10-16" @default.
- W1976307612 title "Synthesis and evaluation of thio-trisaccharides as acceptors for <i>N</i>-acetylglucos-aminyltransferase-V" @default.
- W1976307612 doi "https://doi.org/10.1139/v97-095" @default.
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