Donor-bound glycosylation for various glycosyl acceptors: Bidirectional solid-phase semisynthesis of vancomycin and its derivatives

Takayuki Doi, Atsushi Kinbara, Hitoshi Inoue, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

15 Citations (Scopus)

Abstract

The glycosidation of a polymer-supported glycosyl donor. N-phenyltrifluoroacetimidate, with various glycosyl acceptors is reported. The application of the polymer-supported N-phenyltrifluoroacetimidate is demonstrated in the synthesis of vancomycin derivatives. 2-O-[2-(azidomethyl) benzoyl]glycosyl imidate was attached to a polymer support at the 6-position by a phenylsulfonate linked with a C13 alkyl spacer. Solid-phase glycosidation with a vancomycin aglycon, selective deprotection of the 2-(azidomethyl)-benzoyl group, and glycosylation of the resulting 2-hydroxy group with a vancosamine unit were performed. Nucleophilic cleavage from the polymer support with acetate, chloride, azido, and thioacetate ions provided vancomycin derivatives in pure form after simple purification. The semisynthesis of vancomycin was achieved by deprotection of the acetate derivative.

Original languageEnglish
Pages (from-to)188-198
Number of pages11
JournalChemistry - An Asian Journal
Volume2
Issue number1
DOIs
Publication statusPublished - 2007 Jan 24
Externally publishedYes

Keywords

  • Antibiotics
  • Glycopeptides
  • Glycosylation
  • Solid-phase synthesis
  • Vancomycin

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry

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