Syntheses of depsipeptide analogues of the insect neuropeptide proctolin

Bioorg Med Chem Lett. 2002 Jun 17;12(12):1625-8. doi: 10.1016/s0960-894x(02)00214-7.

Abstract

Four depsipeptide analogues of the insect neuropeptide proctolin (H-Arg-Tyr-Leu-Pro-Thr-OH) have been prepared, containing a single ester linkage between Arg(1) and Tyr(2), Tyr(2) and Leu(3), and between Pro(4) and Thr(5), respectively. A didepsipentapeptide containing an ester linkage between Tyr(2) and Leu(3) and between Pro(4) and Thr(5), has also been prepared. The depsipeptide 4 is the first example of a backbone-modified proctolin analogue which shows full myotropic activity.

MeSH terms

  • Animals
  • Grasshoppers
  • Muscles / drug effects
  • Muscles / physiology
  • Neuropeptides / chemical synthesis*
  • Neuropeptides / chemistry
  • Neuropeptides / pharmacology
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacology

Substances

  • Neuropeptides
  • Oligopeptides
  • proctolin