Synthesis of stapled beta3-peptides through ring-closing metathesis

Org Lett. 2009 Oct 1;11(19):4438-40. doi: 10.1021/ol901803d.

Abstract

The first synthesis of carbon-stapled beta(3)-peptides is reported. The precursor beta(3)-peptides, with O-allyl beta-serines located in an i/i+3 relationship, were prepared on solid phase. We show that efficient ring-closing metathesis (RCM) of these new beta(3)-peptides proceeds smoothly either in solution or on an appropriate solid support. All products were generated with high selectivity for the E-isomer.

MeSH terms

  • Cyclization
  • Peptides / chemical synthesis*
  • Peptides / chemistry
  • Protein Conformation
  • Protein Structure, Secondary

Substances

  • Peptides