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

Robin A. Jeanneret, Charlotte E. Dalton, John M. Gardiner*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

2 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)15063-15078
Number of pages16
JournalJournal of Organic Chemistry
Volume84
Issue number23
DOIs
Publication statusPublished - 6 Dec 2019

Fingerprint

Dive into the research topics of 'Synthesis of Heparan Sulfate- And Dermatan Sulfate-Related Oligosaccharides via Iterative Chemoselective Glycosylation Exploiting Conformationally Disarmed [2.2.2] l -Iduronic Lactone Thioglycosides'. Together they form a unique fingerprint.

Cite this