Jump to main content
Jump to site search

Issue 8, 2001
Previous Article Next Article

Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose

Author affiliations

Abstract

An approach to the synthesis of D-mannopyranose derivatives incorporating an anomeric α-amino acid component is described. An N-acylated bicyclic [2.2.2] lactone, formed via an oxidative ring closure, provides access to a new class of glycopeptide analogues of D-mannopyranose and determines the anomeric configuration of compounds derived therefrom. The mannopyranose diketopiperazine may be equilibrated to the more stable furanose form under basic conditions; in general, mannopyranose derivatives containing an α-amino acid moiety at the anomeric position are less stable than the mannofuranose isomers.

Graphical abstract: Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose

Back to tab navigation

Publication details

The article was received on 09 Dec 2000, accepted on 01 Feb 2001 and first published on 28 Mar 2001


Article type: Paper
DOI: 10.1039/B009940F
Citation: J. Chem. Soc., Perkin Trans. 1, 2001,0, 807-813
  •   Request permissions

    Carbopeptoids: peptides and diketopiperazines incorporating the anomeric centre of mannopyranose

    D. D. Long, R. J. Tennant-Eyles, J. C. Estevez, M. R. Wormald, R. A. Dwek, M. D. Smith and G. W. J. Fleet, J. Chem. Soc., Perkin Trans. 1, 2001, 0, 807
    DOI: 10.1039/B009940F

Search articles by author

Spotlight

Advertisements