Download PDF
Synlett 1997; 1997(4): 395-397
DOI: 10.1055/s-1997-800
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.

Novel Hybrid Morpholino-Glycopeptides with the Amino Acid Nitrogen Replacing C-3 of the Pyranose Ring

Minghui Du, Ole Hindsgaul*
  • *Department of Chemistry, University of Alberta Edmonton, Alberta, CANADA T6G 2G2
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Periodate oxidation of glycopyranosides yields dialdehydes that can be reductively aminated in the presence of amino acids to produce hybrid glycopeptides where the amino acid nitrogen is inserted into the resulting 2,4-dideoxypyranoside at position 3. Nine such 3-morpholino derivatives were prepared, including a disaccharide analog of N-acetyllactosamine (β-Gal(1→4)βGlcNAc) where the nitrogen of glycine was inserted into the galactose ring. The resulting hybrid disaccharide was an excellent substrate for a mild fucosyltransferase which converted it to a novel functionalized LeX mimic.

carbohydrate-peptide hybrids - sugar analogs