| Item type |
文献 / Documents(1) |
| 公開日 |
2023-03-17 |
| アクセス権 |
|
|
アクセス権 |
open access |
| 資源タイプ |
|
|
資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
|
資源タイプ |
journal article |
| 出版社版DOI |
|
|
|
識別子タイプ |
DOI |
|
|
関連識別子 |
https://doi.org/10.1002/chem.202300799 |
|
|
言語 |
ja |
|
|
関連名称 |
10.1002/chem.202300799 |
| 出版タイプ |
|
|
出版タイプ |
AM |
|
出版タイプResource |
http://purl.org/coar/version/c_ab4af688f83e57aa |
| タイトル |
|
|
タイトル |
Residue-selective C−H sulfenylation enabled by acid-activated S-acetamidomethyl cysteine sulfoxide with application to one-pot stapling and lipidation sequence |
|
言語 |
en |
| 著者 |
オオカワチ, ケント
アンザキ, カイト
コバヤシ, ダイシロウ
キャン, リュウジ
ヤスダ, タクマ
傳田, 将也
ハラダ, ノリオ
重永, 章
イナガキ, ノブヤ
大髙, 章
|
| 抄録 |
|
|
内容記述タイプ |
Abstract |
|
内容記述 |
A tyrosine (Tyr)- or tryptophan (Trp)-selective metal-free C−H sulfenylation reaction using an acid-activated Sacetamidomethyl cysteine (Cys) sulfoxide, Cys(Acm)(O), has been achieved. The dually protonated intermediate produced from the Cys(Acm)(O) under acidic conditions allows the sulfenylation of Tyr. Significantly, the reaction in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) mainly affords a Cys-Tyr-linked peptide even in the presence of Trp residues. In contrast, a Cys-Trplinked peptide was selectively obtained from the reaction in the presence of guanidine hydrochloride (Gn·HCl) under acidic conditions. Established Tyr- and Trp-selective sulfenylation methods were used in the Cys-Tyr stapling and Trp-lipidation of glucagon-like peptides 1 in a one-pot/stepwise manner. Investigation of the mechanism showed that orbital- and charge-controlled reactions are responsible for the Trp and Tyr selectivity, respectively. |
|
言語 |
en |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
peptide modification |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
Tyr sulfenylation |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
Trp sulfenylation |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
S-protected cysteine sulfoxide |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
SEAr reaction |
| 書誌情報 |
en : Chemistry- A European Journal
巻 29,
号 26,
p. e202300799,
発行日 2023-03-15
|
| 収録物ID |
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|
収録物識別子タイプ |
ISSN |
|
収録物識別子 |
15213765 |
| 収録物ID |
|
|
収録物識別子タイプ |
NCID |
|
収録物識別子 |
AA11076269 |
| 出版者 |
|
|
出版者 |
Wiley-VCH |
|
言語 |
en |
| 権利情報 |
|
|
言語 |
en |
|
権利情報 |
This is the peer reviewed version of the following article: Ohkawachi, Kento, Anzaki, Kaito, Kobayashi, Daishiro, Kyan, Ryuji, Yasuda, Takuma, Denda, Masaya, Harada, Norio, Shigenaga, Akira, Inagaki, Nobuya, Otaka, Akira, Chem. Eur. J. 2023, 29, 26, e202300799., which has been published in final form at https://doi.org/10.1002/chem.202300799. 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. |
| EID |
|
|
識別子 |
394577 |
|
識別子タイプ |
URI |
| 言語 |
|
|
言語 |
eng |
chemej_29_26_e202300799.pdf (1.16 MB)
