Download PDF
Synlett 2001; 2001(9): 1434-1436
DOI: 10.1055/s-2001-16797
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

One Pot Conversion of Ketoses into Sugar β-Peptides via a Ritter Reaction

Frank Schweizer* , Anders Lohse, Albin Otter, Ole Hindsgaul
  • *Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada; Fax +45-780-492-7705
Further Information

Publication History

Publication Date:
28 August 2001 (online)

  PDF Download  Permissions and Reprints All articles of this category

α-d-Galacto-2-deoxy-oct-3-ulopyranosonic acids can be converted into unnatural glycopeptides via a one pot intramolecular Ritter reaction. Initially, the ketopyranoside reacts under Lewis acid catalyzed conditions with a nitrile (aromatic or aliphatic) to form a glycosylimino anhydride intermediate which can be isolated. Exposure of this intermediate to simple priamary amines or amino acids produces novel sugar-β-peptides. Three different nitriles and three different amines have been used to generate 6 sugar β-peptides to demonstrate the generality of this reaction.

carbohydrates - combinatorial chemistry - glycopeptides - glycosylamides

      >