Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups

Hiroshi Tanaka, Yuki Iwata, Daisuke Takahashi, Masaatsu Adachi, Takashi Takahashi

Research output: Contribution to journalArticlepeer-review

61 Citations (Scopus)

Abstract

The efficient and elegant synthesis of N-glycosides by N-glycosylation of asparagine-containing peptides is described. Glycosylation of primary amides with glycosyl N-phenyltrifluoroimidates in the presence of a catalytic amount of TMSOTf in nitromethane smoothly proceeded to provide the corresponding N-glycosyl amino acids in excellent yields. This coupling method was adaptable to the coupling of various glycosyl donors with amino acids and peptides.

Original languageEnglish
Pages (from-to)1630-1631
Number of pages2
JournalJournal of the American Chemical Society
Volume127
Issue number6
DOIs
Publication statusPublished - 2005 Feb 16
Externally publishedYes

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Efficient stereoselective synthesis of γ-N-glycosyl asparagines by N-glycosylation of primary amide groups'. Together they form a unique fingerprint.

Cite this