Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 129, Issue 33, Pages 10064-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja072804l
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Synthesis of erythro-N-Boc-beta-mercapto-L-phenylalanine enables native chemical ligation at phenylalanine. In the form of the S-ethyldisulfanyl derivative, the N-Boc amino acid is used to cap a tetrapeptide generated by Fmoc-SPPS. The native chemical ligation with C-terminal thioesters then occurs successfully and is followed by selective desulfurization of the benzylic C-S bond. The method is applied to the synthesis of LYRAMFRANK, thereby establishing compatibility with the reactive side chains and the ability to ligate other than glycine.
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