Syntheses of p-nitrophenyl 3- and 4-thio-β-D-glycopyranosides.
Thioglycosides have proved to be useful, enzymatically stable analogs of glycosides for structural and mechanistic studies and their synthesis is considerably simplified through the use of thioglycoligases. As part of an investigation into the use of thioglycosides as potential pharmacological chaperones, and as components of glycoproteins and glycolipids, the syntheses of p-nitrophenyl 3-thio-β-D-galactopyranoside, phenyl 1,4-dithio-β-D-glucopyranoside, p-nitrophenyl 4-thio-β-D-mannopyranoside and p-nitrophenyl 2-acetamido-2-deoxy-4-thio-β-D-mannopyranoside are described.
Department of Chemistry, The University of British Columbia, 2036 Main Mall, Vancouver, British Columbia, Canada V6T 1Z1.
Hong-Ming
HM
Chen
Stephen G
SG
Withers
D002240:Carbohydrate Sequence; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013865:Thioglycosides / Q000138:chemical synthesis* / Q000737:chemistry*; D054330:Thiosugars / Q000138:chemical synthesis* / Q000737:chemistry*
D013865:Thioglycosides; D054330:Thiosugars