Synthesis of peptide .alpha.-thioesters
- Livermore, CA
- Clayton, CA
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.
- Research Organization:
- Lawrence Livermore National Laboratory (LLNL), Livermore, CA
- Sponsoring Organization:
- United States Department of Energy
- DOE Contract Number:
- W-7405-ENG-48
- Assignee:
- Lawrence Livermore National Security, LLC (Livermore, CA)
- Patent Number(s):
- 7,414,106
- Application Number:
- 10/871,346
- OSTI ID:
- 943347
- Country of Publication:
- United States
- Language:
- English
Peptide Syntheses Via Amino Acid Active Esters 1
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journal | August 1959 |
Solid-Phase Synthesis of Lipidated Peptides
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journal | May 2002 |
Biosynthesis of a Head-to-Tail Cyclized Protein with Improved Biological Activity
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journal | June 1999 |
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