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Synlett 2001; 2001(9): 1434-1436
DOI: 10.1055/s-2001-16797
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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
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Publikationsdatum:
28. August 2001 (online)

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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