Synthesis of α-GalNAc Thioconjugates from an α-GalNAc Mercaptan
- 11 April 2002
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 67 (9) , 2995-2999
- https://doi.org/10.1021/jo0110909
Abstract
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.Keywords
This publication has 15 references indexed in Scilit:
- Elaboration of a novel type of interglycosidic linkage: syntheses of disulfide disaccharidesTetrahedron Letters, 2001
- Thiosugars Iii. Stereoselective Approach to β-(1→2)-2,3-Dideoxy-2-C-Acetamidomethyl-2-S-Thiodisaccharides From LevoglucosenoneJournal of Carbohydrate Chemistry, 2000
- Synthesis and Immunostimulating Activity of A Thioglycolipopeptide Glycomimetic As A Potential Anticancer Vaccine Derived From Tn AntigenJournal of Carbohydrate Chemistry, 2000
- Efficient synthesis of thioglycosides via a Mitsunobu condensationTetrahedron Letters, 1999
- NAG-thiazoline, An N-Acetyl-β-hexosaminidase Inhibitor That Implicates Acetamido ParticipationJournal of the American Chemical Society, 1996
- Synthesis and Evaluation as Irreversible Glycosidase Inhibitors of Mono‐ and Oligo(glycosylthio)benzoquinonesHelvetica Chimica Acta, 1994
- Réduction-acetylation sélective des azido-sucres par le mélange acide thioacétique-thioacétate de potassiumCarbohydrate Research, 1990
- Free-radical addition of 1-thiosugars to alkenes a new general approach to the synthesis of 1-thioglycosidesTetrahedron Letters, 1988
- Preparation of anomeric pairs of 1-thioglycosides: use of anomerization catalyzed by boron trifluorideCarbohydrate Research, 1980
- Equilibrium Constants for the Demetalation of Iron PorphyrinsThe Journal of Organic Chemistry, 1963