Synthesis of 1,2-dithiolane analogues of leucine for potential use in peptide chemistry

Org Lett. 2002 Apr 4;4(7):1139-42. doi: 10.1021/ol0255458.

Abstract

[reaction: see text]1,2-Dithiolanes present several points of interest for both peptide and medicinal chemistry, yet no chiral alpha-amino acids containing this five-membered heterocyclic system are available. We report here the first synthesis of N- and C-protected derivative of (S)-2-amino-3-(1,2-dithiolan-4-yl)propionic acid (Adp) and its 1,3-dithiolic form.

MeSH terms

  • Indicators and Reagents
  • Leucine / analogs & derivatives*
  • Leucine / chemical synthesis*
  • Peptides / chemistry*
  • Stereoisomerism
  • Thioctic Acid / analogs & derivatives
  • Thioctic Acid / chemistry*

Substances

  • 1,2-dithiolane
  • Indicators and Reagents
  • Peptides
  • Thioctic Acid
  • Leucine