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ID 119333
Author
Hidaka, Kota Tokushima University
Kobayashi, Daishiro Tokushima University
Hayashi, Junya Tokushima University
Keywords
S-protected cysteine sulfoxide
stepwise disulfide formation
insulin
S-chlorocysteine
peptide lipidation
Content Type
Journal Article
Description
An advanced insulin synthesis is presented that utilizes one-pot/stepwise disulfide bond formation enabled by acid-activated S-protected cysteine sulfoxides in the presence of chloride anion. S-chlorocysteine generated from cysteine sulfoxides reacts with an S-protected cysteine to afford S-sulfenylsulfonium cation, which then furnishes the disulfide or reversely returns to the starting materials depending on the S-protection employed and the reaction conditions. Use of S-acetamidomethyl cysteine (Cys(Acm)) and its sulfoxide (Cys(Acm)(O)) selectively give the disulfide under weak acid conditions in the presence of MgCl2 even if S-p-methoxybenzyl cysteine (Cys(MBzl)) and its sulfoxide (Cys(MBzl)(O)) are also present. In contrast, the S-MBzl pair yields the disulfide under more acidic conditions in the presence of a chloride anion source. These reaction conditions allowed a one-pot insulin synthesis. Additionally, lipidated insulin was prepared by a one-pot disulfide-bonding/lipidation sequence.
Journal Title
Chemistry- A European Journal
ISSN
15213765
NCID
AA11076269
Publisher
Wiley-VCH
Start Page
e202401003
Published Date
2024-04-29
Remark
論文本文は2025-05-23以降公開予定
This is the peer reviewed version of the following article: Kota Hidaka, Daishiro Kobayashi, Junya Hayashi, Masaya Denda, Akira Otaka, e202401003., which has been published in final form at https://doi.org/10.1002/chem.202401003. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.
EDB ID
DOI (Published Version)
URL ( Publisher's Version )
language
eng
TextVersion
その他
departments
Pharmaceutical Sciences