skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Synthesis of peptide .alpha.-thioesters

Abstract

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.

Inventors:
 [1];  [1];  [2]
  1. Livermore, CA
  2. Clayton, CA
Publication Date:
Research Org.:
Lawrence Livermore National Lab. (LLNL), Livermore, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
943347
Patent Number(s):
7,414,106
Application Number:
10/871,346
Assignee:
Lawrence Livermore National Security, LLC (Livermore, CA)
DOE Contract Number:  
W-7405-ENG-48
Resource Type:
Patent
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Camarero, Julio A, Mitchell, Alexander R, and De Yoreo, James J. Synthesis of peptide .alpha.-thioesters. United States: N. p., 2008. Web.
Camarero, Julio A, Mitchell, Alexander R, & De Yoreo, James J. Synthesis of peptide .alpha.-thioesters. United States.
Camarero, Julio A, Mitchell, Alexander R, and De Yoreo, James J. Tue . "Synthesis of peptide .alpha.-thioesters". United States. https://www.osti.gov/servlets/purl/943347.
@article{osti_943347,
title = {Synthesis of peptide .alpha.-thioesters},
author = {Camarero, Julio A and Mitchell, Alexander R and De Yoreo, James J},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2008},
month = {8}
}

Patent:

Save / Share: