Synthesis of alpha-GalNAc thioconjugates from an alpha-GalNAc mercaptan.
A variety of functionalized thioglycosides and other derivatives (10-24) of 2-acetamido-2-deoxy-1-thio-alpha-D-galactopyranose have been prepared in good yields and with high anomeric purities by S-substitution reactions of the sulfide anion or sulfur-centered radical from mercaptan 6. Given the importance in nature of the alpha-GalNAc 1-O-linkage, and the greater chemical and biological stability of the corresponding 1-S-linkage, these thioconjugates may find application in studies of synthetic vaccines, enzyme inhibitors, glycomimetic scaffolds, and other complex carbohydrate systems.
Knapp
Spencer
S
Department of Chemistry & Chemical Biology, Rutgers-The State University of New Jersey, 610 Taylor Road, Piscataway, New Jersey 08854-8087, USA. knapp@rutchem.rutgers.edu
Myers
David S
DS
D000475:Alkenes / Q000737:chemistry; D000478:Alkylation; D015295:Antigens, Tumor-Associated, Carbohydrate; D002384:Catalysis; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis; D013862:Thiogalactosides / Q000138:chemical synthesis* / Q000737:chemistry*
C463720:2-acetamido-2-deoxy-1-thio-alpha-D-galactopyranose; C463719:2-acetamido-2-deoxy-2,3,4-tri-O-acetyl-1-thio-alpha-D-galactopyranose; D000475:Alkenes; D015295:Antigens, Tumor-Associated, Carbohydrate; D013438:Sulfhydryl Compounds; D013862:Thiogalactosides; C040286:Tn antigen