ID 111883
Author
Tsuda, Yusuke Tokushima University
Tsuji, Kohei Tokushima University
Denda, Masaya Tokushima University
Sato, Kohei Tokushima University
Kitakaze, Keisuke Tokushima University
Nakamura, Takahiro Tokushima University
Keywords
acyl transfer
native chemical ligation
nickel(II)-mediated alcoholysis
peptide hydrazides
peptide thioesters
Content Type
Journal Article
Description
Peptide thioesters are very useful in protein chemistry, and chemistry- and biochemistry-based protocols are used for the preparation of thioesters. Among such protocols, only a few biochemistry-based approaches have been use for naturally occurring peptide sequences. The development of chemistry-based protocols applicable to natural sequences remains a challenge, and the development of such methods would be a major contribution to protein science. Here, we describe the preparation of peptide thioesters using innovative methodology that features nickel(II)-mediated alcoholysis of a naturally occurring peptide sequence, followed by O-N and N-S acyl transfers. This protocol involves sequential quadruple acyl transfer, termed SQAT. Notably, the SQAT system consists of sequential chemical reactions that allow naturally occurring peptide sequences to be converted to thioesters without requiring an artificial chemical unit.
Journal Title
Chemistry Open
ISSN
21911363
Publisher
WILEY-VCH Verlag GmbH & Co. KGaA
Volume
4
Issue
4
Start Page
448
End Page
452
Published Date
2015-04-28
Rights
🄫2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution-NonCommercial-NoDerivs License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non-commercial and no modifications or adaptations are made.
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
FullText File
language
eng
TextVersion
Publisher
departments
Pharmaceutical Sciences