Synthesis of Peptides Containing C-Terminal Methyl Esters Using Trityl Side-Chain Anchoring: Application to the Synthesis of a-Factor and a-Factor Analogs

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• 作者：Veronica Diaz-Rodriguez ; Daniel G. Mullen ; Elena Ganusova ; Jeffrey M. Becker ; Mark D. Distefano
• 刊名：Organic Letters
• 出版年：2012
• 出版时间：November 16, 2012
• 年：2012
• 卷：14
• 期：22
• 页码：5648-5651
• 全文大小：242K
• 年卷期：v.14,no.22(November 16, 2012)
• ISSN：1523-7052

文摘

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.