Synthesis of Heparan Sulfate- and Dermatan Sulfate-Related Oligosaccharides via Iterative Chemoselective Glycosylation Exploiting Conformationally Disarmed [2.2.2] l-Iduronic Lactone Thioglycosides.

Abstract

Heparan sulfate (HS) and dermatan sulfate (DS) are l-iduronic acid containing glycosaminoglycans (GAGs) which are implicated in a number of biological processes and conditions including cancer and viral infection. Chemical synthesis of HS and DS is required to generate structurally defined oligosaccharides for a biological study. Herein, we present a new synthetic approach to HS and DS oligosaccharides using chemoselective glycosylation which relies on a disarmed [2.2.2] l-ido lactone motif. The strategy provides a general approach for iterative-reducing end chain extension, using only shelf-stable thioglycoside building blocks, exploiting a conformational switch to control reactivity, and thus requires no anomeric manipulation steps between glycosylations.

• Authors: Robin A Jeanneret, Charlotte E Dalton, John M Gardiner
• Journal: The Journal of organic chemistry (J Org Chem) Vol. 84 Issue 23 Pg. 15063-15078 (12 06 2019) ISSN: 1520-6904 [Electronic] United States
• PMID: 31674785 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Lactones
• Oligosaccharides
• Sulfates
• Thioglycosides
• Dermatan Sulfate
• Iduronic Acid

Topics

• Carbohydrate Conformation
• Dermatan Sulfate (chemistry)
• Glycosylation
• Iduronic Acid (chemistry)
• Lactones (chemistry)
• Oligosaccharides (chemical synthesis, chemistry)
• Sulfates (chemistry)
• Thioglycosides (chemistry)