3-Azidoazetidines as the first scaffolds for β-amino azetidine carboxylic acid peptidomimetics: azetidine iminosugars containing an acetamido group do not inhibit β-N-acetylhexosaminidases

Zilei Liu, Sarah F. Jenkinson, Atsushi Kato, Shinpei Nakagawa, Mark R. Wormald, Chu Yi Yu, George W.J. Fleet*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Stable amides and oligopeptides derived from methyl trans,trans-3-azido-4-hydroxymethyl-L-azetidine carboxylate, prepared in 19% yield from diacetone allose, is the first example of a β-amino-azetidine carboxylic acid incorporated into peptidomimetics and provides a scaffold for investigating secondary structure induced by a novel β-amino acid. A number of azetidine iminosugars containing a NHAc substituent were prepared but none of them were β-N-acetylhexosaminidase inhibitors.

Original languageEnglish
Pages (from-to)872-881
Number of pages10
JournalTetrahedron Asymmetry
Volume27
Issue number17-18
DOIs
StatePublished - 2016

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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