Total Synthesis of the Highly N-Methylated Peptide Jahanyne

J Org Chem. 2018 Jun 15;83(12):6741-6747. doi: 10.1021/acs.joc.8b00503. Epub 2018 Jun 7.

Abstract

Total synthesis of jahanyne (1) was achieved from commercially available materials on a 38 mg scale. The Boc- N-Me- L-Val-OH fragment along with the HATU/DIPEA coupling condition was applied to avoid the diketopiperazine side reaction in solution phase synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diketopiperazines / chemistry
  • HeLa Cells
  • Humans
  • Lipopeptides / chemical synthesis*
  • Lipopeptides / chemistry
  • Methylation
  • Spectrum Analysis / methods

Substances

  • Diketopiperazines
  • Lipopeptides
  • jahanyne