Synthesis of peptides containing C -terminal methyl esters using trityl side-chain anchoring: Application to the synthesis of a-factor and a-factor analogs

Veronica Diaz-Rodriguez, Daniel G. Mullen, Elena Ganusova, Jeffrey M. Becker, Mark D. Distefano

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24 Scopus citations

Abstract

A new cysteine anchoring method was developed for the synthesis of peptides containing C-terminal cysteine methyl esters. This method consists of attachment of Fmoc-Cys-OCH3 to either 2-ClTrt-Cl or Trt-Cl resins (via the side-chain thiol) followed by preparation of the desired peptide using Fmoc-based SPPS. We applied this method to the synthesis of the mating pheromone a-factor and a 5-FAM labeled a-factor analog. The peptides were obtained with high yield and purity and were shown to be bioactive in a growth arrest assay.

Original languageEnglish (US)
Pages (from-to)5648-5651
Number of pages4
JournalOrganic Letters
Volume14
Issue number22
DOIs
StatePublished - Nov 16 2012

Bibliographical note

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Copyright 2013 Elsevier B.V., All rights reserved.

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