Alkylated sugar amino acids: a new entry toward highly functionalized dipeptide isosters

Org Lett. 2004 Sep 2;6(18):3167-70. doi: 10.1021/ol048750r.

Abstract

[reaction: see text] Novel highly functionalized dipeptide isosters are synthesized via a diastereoselective alkyl/arylation protocol of a glucose-derived (R)-tert-butanesulfinylimine. One of these novel sugar amino acid derivatives, a D-Ala-Ser/Thr isostere, was applied in a peptide synthesis protocol to afford a cyclic tetramer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Catalysis
  • Cyclization
  • Dipeptides / chemical synthesis*
  • Dipeptides / chemistry
  • Indicators and Reagents
  • Molecular Structure
  • Peptides, Cyclic / chemical synthesis*
  • Peptides, Cyclic / chemistry
  • Stereoisomerism
  • Sugar Acids / chemistry*

Substances

  • Amino Acids
  • Dipeptides
  • Indicators and Reagents
  • Peptides, Cyclic
  • Sugar Acids