Total Synthesis of a Structurally Complex Tetrasaccharide Repeating Unit of Vibrio cholerae O43

Org Lett. 2023 Sep 1;25(34):6413-6418. doi: 10.1021/acs.orglett.3c02430. Epub 2023 Aug 21.

Abstract

Herein we report the first total synthesis of a densely functionalized tetrasaccharide repeating unit of Vibrio cholerae O43, which contains rare deoxy amino sugars d-quinovosamine and d-viosamine attached with the rare amino acid N-acetyl-l-allothreonine. Synthesis of orthogonally protected rare sugars and unnatural amino acid building blocks, stereoselective construction of three consecutive 1,2-cis glycosidic linkages, amide coupling, and the presence of five nitrogen atoms dispersed over four sugar units as well as the carboxylic acid functionality make the total synthesis a formidable task.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides
  • Amino Acids
  • Amino Sugars
  • Oligosaccharides*
  • Vibrio cholerae*

Substances

  • Oligosaccharides
  • Amides
  • Amino Acids
  • Amino Sugars