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ID 119333
著者
Hidaka, Kota Tokushima University
Kobayashi, Daishiro Tokushima University
Hayashi, Junya Tokushima University
キーワード
S-protected cysteine sulfoxide
stepwise disulfide formation
insulin
S-chlorocysteine
peptide lipidation
資料タイプ
学術雑誌論文
抄録
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.
掲載誌名
Chemistry- A European Journal
ISSN
15213765
cat書誌ID
AA11076269
出版者
Wiley-VCH
開始ページ
e202401003
発行日
2024-04-29
備考
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.
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言語
eng
著者版フラグ
その他
部局
薬学系