Direct conversion of resin-bound peptides to C-terminal esters

Org Lett. 2010 Apr 16;12(8):1852-5. doi: 10.1021/ol100471k.

Abstract

A mild and effective method was developed to convert peptides immobilized on the 2-chlorotrityl and Wang resins directly to C-terminal esters. After conventional Fmoc peptide synthesis, treatment with anhydrous HCl (0.2-3 M) in a variety of alcohols was shown to produce the corresponding peptide esters in good yield and purity. Under the mildest conditions investigated, acid-sensitive protection groups such as N-Boc, trityl, tert-butyl ether, tert-butyl ester, and Pbf remain intact.

MeSH terms

  • Esterification
  • Esters / chemistry*
  • Peptides / chemistry*
  • Resins, Synthetic / chemistry*

Substances

  • Esters
  • Peptides
  • Resins, Synthetic