Fmoc-based synthesis of peptide thioesters for native chemical ligation employing a tert-butyl thiol linker

Richard Raz; Jörg Rademann

doi:10.1021/ol1029723

Fmoc-based synthesis of peptide thioesters for native chemical ligation employing a tert-butyl thiol linker

Org Lett. 2011 Apr 1;13(7):1606-9. doi: 10.1021/ol1029723. Epub 2011 Feb 28.

Authors

Richard Raz¹, Jörg Rademann

Affiliation

¹ Leibniz Institute of Molecular Pharmacology (FMP), 13125, Germany.

PMID: 21355617
DOI: 10.1021/ol1029723

Abstract

tert-Butyl thioesters display an astonishing stability toward secondary amines in basic milieu, in contrast to other alkyl and aryl thioesters. Exploiting this enhanced stability, peptide thioesters were synthesized in a direct manner, applying a tert-butyl thiol linker for Fmoc-based solid-phase peptide synthesis.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Esters / chemical synthesis*
Molecular Structure
Peptides / chemistry*
Sulfhydryl Compounds / chemistry*

Substances

Esters
Peptides
Sulfhydryl Compounds
tert-butylthiol