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ID 114733
Author
Ohkawachi, Kento Tokushima University
Kobayashi, Daishiro Tokushima University
Morimoto, Kyohei Tokushima University
Yamatsugu, Kenzo The University of Tokyo
Kanai, Motomu The University of Tokyo
Content Type
Journal Article
Description
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.
Journal Title
Organic Letters
ISSN
15237060
15237052
NCID
AA11347843
AA1218968X
Publisher
ACS Publications
Volume
22
Issue
14
Start Page
5289
End Page
5293
Published Date
2020-05-12
Rights
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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DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Author
departments
Pharmaceutical Sciences