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Synthesis of peptide .alpha.-thioesters

United States Patent

August 19, 2008
View the Complete Patent at the US Patent & Trademark Office
Lawrence Livermore National Laboratory - Visit the Industrial Partnerships Office Website
Disclosed herein is a new method for the solid phase peptide synthesis (SPPS) of C-terminal peptide .alpha. thioesters using Fmoc/t-Bu chemistry. This method is based on the use of an aryl hydrazine linker, which is totally stable to conditions required for Fmoc-SPPS. When the peptide synthesis has been completed, activation of the linker is achieved by mild oxidation. The oxidation step converts the acyl-hydrazine group into a highly reactive acyl-diazene intermediate which reacts with an .alpha.-amino acid alkylthioester (H-AA-SR) to yield the corresponding peptide .alpha.-thioester in good yield. A variety of peptide thioesters, cyclic peptides and a fully functional Src homology 3 (SH3) protein domain have been successfully prepared.
Camarero; Julio A. (Livermore, CA), Mitchell; Alexander R. (Livermore, CA), De Yoreo; James J. (Clayton, CA)
Lawrence Livermore National Security, LLC (Livermore, CA)
10/ 871,346
June 18, 2004
The United States Government has rights in this invention pursuant to Contract No. W-7405-ENG-48 between the United States Department of Energy and The University of California for the operation of Lawrence Livermore National Laboratory.