Synthesis of a galacto-configured C-ketoside-based gamma-sugar-amino acid and its use in peptide coupling reactions.
Gamma-sugar-amino acid analogues in the form of C-ketosides can be prepared in 5-6 steps starting from D-galactono-1,5-lactone. The key step in the synthesis is the trimethylsilyl trifluoromethanesulfonate (TMSOTf) promoted C-glycosylation of 2-deoxy-3-ulopyranosonates with trimethylsilyl cyanide. Hydrogenation of the resulting beta-cyano esters provides C-ketoside-based gamma-sugar-amino acids that serve as building blocks for the synthesis of unnatural neoglycopeptides.
Schweizer
Frank
F
Department of Chemistry, University of Manitoba, Winnipeg, Manitoba, Canada R3T 2N2. schweize@cc.umanitoba.ca
Hindsgaul
Ole
O
D000596:Amino Acids / Q000737:chemistry; D006020:Glycopeptides / Q000138:chemical synthesis*; D010455:Peptides / Q000138:chemical synthesis*; D013400:Sugar Acids / Q000737:chemistry
D000596:Amino Acids; D006020:Glycopeptides; D010455:Peptides; D013400:Sugar Acids