Ohkawachi, Kento Tokushima University
Kobayashi, Daishiro Tokushima University
Morimoto, Kyohei Tokushima University
Yamatsugu, Kenzo The University of Tokyo
Kanai, Motomu The University of Tokyo
Sulfanylmethyl-installed dimethylaminopyridine, 2-sulfanylmethyl-4-dimthylaminopyridine (SMDMAP) (2), has an acidic thiol group comparable to that in aryl thiols due to the formation of a zwitterion consisting of a thiolate anion and a pyridinium cation. It can be used as an additive for native chemical ligation. The alkyl thiol in 2 allows it to be used for the one-pot/NCL–desulfurization protocol in peptide synthesis. The utility of 2 in the synthesis of cyclic peptides is demonstrated.
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.0c01383.
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