Synthesis of glycolipid antigens

Suvarn S. Kulkarni, Jacquelyn Gervay-Hague

Research output: Chapter in Book/Report/Conference proceedingConference contribution

4 Scopus citations

Abstract

Carbohydrates and glycoconjugates play important roles in complex life processes. Development of carbohydrate-based therapeutics is a major focus of our laboratory requiring the synthesis of glycolipid antigens for biological evaluation. Stereoselective formation of O- and C-glycosides is one of the central challenges in carbohydrate synthesis. In this pursuit, we employ glycosyl iodides as unique glycosyl donors to construct functionally enriched appendages on the anomeric center of the sugar moiety in a highly efficient and stereoselective manner. These constructs can be used to rapidly synthesize a panoply of glycoside analogs for biological studies. In this minireview, glycosyl iodide mediated syntheses of α-linked O-glycolipids such as KRN 7000 and BbGL2 as well C-glycolipid analogs are described.

Original languageEnglish (US)
Title of host publicationACS Symposium Series
PublisherAmerican Chemical Society
Pages153-166
Number of pages14
Volume990
ISBN (Print)9780841274402
DOIs
Publication statusPublished - Sep 1 2008

Publication series

NameACS Symposium Series
Volume990
ISSN (Print)00976156
ISSN (Electronic)19475918

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ASJC Scopus subject areas

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Kulkarni, S. S., & Gervay-Hague, J. (2008). Synthesis of glycolipid antigens. In ACS Symposium Series (Vol. 990, pp. 153-166). (ACS Symposium Series; Vol. 990). American Chemical Society. https://doi.org/10.1021/bk-2008-0990.ch007