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Proc Natl Acad Sci U S A. 1995 Dec 19;92(26):12485-9.

Peptide synthesis using unprotected peptides through orthogonal coupling methods.

Author information

1
Department of Microbiology and Immunology, Vanderbilt University, Nashville, TN 37232-2363, USA.

Abstract

We describe an approach to the synthesis of peptides from segments bearing no protecting groups through an orthogonal coupling method to capture the acyl segment as a thioester that then undergoes an intramolecular acyl transfer to the amine component with formation of a peptide bond. Two orthogonal coupling methods to give the covalent ester intermediate were achieved by either a thiol-thioester exchange mediated by a trialkylphosphine and an alkylthiol or a thioesterification by C alpha-thiocarboxylic acid reacting with a beta-bromo amino acid. With this approach, unprotected segments ranging from 4 to 37 residues were coupled to aqueous solution to give free peptides up to 54 residues long with high efficiency.

PMID:
8618926
PMCID:
PMC40382
[Indexed for MEDLINE]
Free PMC Article
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