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ID 117175
Author
Kobayashi, Daishiro Tokushima University
Kuraoka, Eisuke Tokushima University
Hayashi, Junya Tokushima University
Yasuda, Takuma Kyoto University
Kohmura, Yutaka Tokushima University
Harada, Norio Kyoto University
Inagaki, Nobuya Kyoto University
Keywords
C−H sulfenylation of indole
tryptophan-selective modification
S-protected cysteine sulfoxide
peptide lipidation
glucagon-like peptides
Content Type
Journal Article
Description
Lipidation of peptides is a promising means of modification that can improve the therapeutic character of biologically active peptides. Here a novel lipidation protocol for peptides is described. The C−H sulfenylation of indole in peptides using S-p-methoxybenzyl cysteine sulfoxide under acidic conditions in the presence of ammonium chloride, anisole and triisopropylsilane enables late-stage tryptophan-selective peptide lipidation. This developed protocol has been used successfully for the lipidation of glucagon-like peptides. Oral glucose tolerance tests in wild-type mice indicated that the resulting lipidated peptides stimulate insulin secretion and exhibit a more long-lasting blood-glucose-lowering effect than a parent non-lipidated peptide.
Journal Title
ACS Medicinal Chemistry Letters
ISSN
19485875
NCID
AA12599965
Publisher
ACS Publications
Volume
13
Issue
7
Start Page
1125
End Page
1130
Published Date
2022-06-14
Rights
This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS Medicinal Chemistry 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/acsmedchemlett.2c00161.
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Author
departments
Pharmaceutical Sciences