Naruse, Naoto Tokushima University
Ohkawachi, Kento Tokushima University
Inokuma, Tsubasa Tokushima University Tokushima University Educator and Researcher Directory KAKEN Search Researchers
Otaka, Akira Tokushima University Tokushima University Educator and Researcher Directory KAKEN Search Researchers
Resin-bound N–sulfanylethylanilide (SEAlide) peptide was found to function as a crypto-thioester peptide. Exposure of the peptide resin to an aqueous solution under neutral conditions in the presence of thiols affords thioesters without accompanying racemization of C-terminal amino acids. Furthermore, the resin-bound SEAlide peptides react with N-terminal cysteinyl peptides in the absence of phosphate salts to afford ligated products, whereas soluble SEAlide peptides do not. This unexpected difference in reactivity of the SEAlide peptides allows for a one-pot/three-fragment ligation using resin-bound and unbound peptides.
This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright ©American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see https://doi.org/10.1021/acs.orglett.8b00795.
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orglett_20_8_2449.pdf 790 KB
orglett_20_8_2449_si.pdf 553 KB