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Synlett 1998; 1998(4): 393-395
DOI: 10.1055/s-1998-1660
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A Novel Versatile Glycosyl α-Aminoacid Derivative for Glycopeptidic Chemistry

Philippe Coutrot* , Claude Grison, Frédéric Coutrot
  • *Laboratoire de Chimie Organique 2, UMR CNRS 7565, INCM, Université Henri Poincaré, Nancy 1, 54506 Vandoeuvre-les-Nancy, France; Fax Int.+ 03 83 91 23 93; E-mail: coutrot@incm.u.nancy.fr
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Publication History

Publication Date:
31 December 2000 (online)

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The chain extension with an α-ketoester unit at C-6 of 1,2:3,4-di-O-isopropylidene-α-D-galacto-hexodialdo-1,5-pyranose 1 followed by a catalytic reductive amination of the α-keto group led to the novel protected 2-(1′,2′:3′,4′-di-O-isopropylidene-6′-deoxy-α-D-galactopyranosyl) glycine diastereomers 6 and 6′ which are easy to separate. Chemoselective removal of N- or C-protecting groups at the α-aminoacid moiety allowed subsequent insertion of these 6-deoxy-α-D-galactopyranosyl glycine residues into a peptide chain.

glycosyl α-aminoacid - glycopeptides - α-ketoester - galactosyl glycine - α-chloroglycidic ester