Synthesis and Utility of β‑Selenophenylalanine and β‑Selenoleucine in Diselenide–Selenoester Ligation

The synthesis of suitably protected β-selenophenylalanine and β-selenoleucine amino acids was accomplished from Garner’s aldehyde as a common starting point. These selenoamino acids were incorporated into model peptides and shown to facilitate rapid diselenide–selenoester ligation (DSL) with peptide...

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Bibliographic Details
Published in:Journal of organic chemistry 2020-02, Vol.85 (3), p.1567-1578
Main Authors: Wang, Xiaoyi, Corcilius, Leo, Premdjee, Bhavesh, Payne, Richard J
Format: Article
Language:English
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Summary:The synthesis of suitably protected β-selenophenylalanine and β-selenoleucine amino acids was accomplished from Garner’s aldehyde as a common starting point. These selenoamino acids were incorporated into model peptides and shown to facilitate rapid diselenide–selenoester ligation (DSL) with peptide selenoesters which, when coupled with in situ deselenization, afforded native peptide products. The utility of one-pot DSL–deselenization chemistry at phenylalanine and leucine was demonstrated through the rapid synthesis of a glycosylated interferon-γ fragment and the chemokine-binding protein UL22A, respectively.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02665