Syntheses of the 3- and 4-thio analogues of 4-nitrophenyl 2-acetamido-2-deoxy-beta-D-gluco- and galactopyranoside.
The syntheses of 4-nitrophenyl beta-glycosides of the 3-thio and 4-thio analogues of the two principal 2-acetamido-2-deoxy-hexoses found in living systems, GlcNAc and GalNAc, are described. While synthesis of the 4-thio analogues could be achieved via nucleophilic displacements of sulfonate derivatives with thioacetate, problems with neighbouring group acetamido participation necessitated the use of sulfamidate intermediates for the 3-thio analogues. These 3- and 4-thio analogues are employed in the chemo-enzymatic synthesis of thio-oligosaccharide analogues of structures present in glycosaminoglycans, glycoproteins and glycolipids.
Chen
Hong-Ming
HM
Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
Withers
Stephen G
SG
D000085:Acetates / Q000737:chemistry; D000116:Acetylgalactosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002241:Carbohydrates / Q000737:chemistry; D002621:Chemistry / Q000379:methods; D005690:Galactose / Q000737:chemistry*; D008956:Models, Chemical; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry
D000085:Acetates; D002241:Carbohydrates; D009844:Oligosaccharides; C014123:4-nitrophenyl-2-acetamido-2-deoxygalactopyranoside; C014124:4-nitrophenyl-N-acetyl-2-deoxyglucopyranoside; D000116:Acetylgalactosamine; D000117:Acetylglucosamine; D005690:Galactose