| Item type |
文献 / Documents(1) |
| 公開日 |
2018-07-26 |
| アクセス権 |
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|
アクセス権 |
open access |
| 資源タイプ |
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|
資源タイプ識別子 |
http://purl.org/coar/resource_type/c_6501 |
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資源タイプ |
journal article |
| 出版社版DOI |
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|
識別子タイプ |
DOI |
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|
関連識別子 |
https://doi.org/10.1002/bip.22757 |
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言語 |
ja |
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|
関連名称 |
10.1002/bip.22757 |
| 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 |
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|
タイトル |
Preparation of Peptide Thioesters from Naturally Occurring Sequences Using Reaction Sequence Consisting of Regioselective S-Cyanylation and Hydrazinolysis |
|
言語 |
en |
| 著者 |
ミヤジマ, リン
ツダ, ユウスケ
猪熊, 翼
重永, 章
イマニシ, ミキ
フタキ, シロウ
大髙, 章
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| 抄録 |
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内容記述タイプ |
Abstract |
|
内容記述 |
Vital roles of peptide/protein thioesters in protein chemistry, including chemical or semi synthesis of proteins, have encouraged studies on the development of methods for the preparation of such chemical units. Biochemical protocols using intein or sortase have proved to be useful in protein chemistry as methods suitable for naturally occurring sequences, including recombinant proteins. Although chemical protocols are potential options for thioester preparation, only a few are applicable to naturally occurring sequences, because standard chemical protocols require an artificial chemical device for producing thioesters. In this context, the chemical preparation of thioesters based on a reaction sequence consisting of regioselective S-cyanylation and hydrazinolysis was investigated. Regioselective S-cyanylation, which is required for cysteine-containing thioesters, was achieved with the aid of zinc-complex formation of a CCHH-type zinc-finger sequence. Free cysteine residues that are not involved in complex formation were selectively protected with a 6-nitroveratryl group followed by S-cyanylation of the zinc-binding cysteine. Hydrazinolysis of the resulting S-cyanopeptideand subsequent photo-removal of the 6-nitroveratryl group yielded the desired peptide hydrazide, which was then converted to the corresponding thioester. The generated thioester was successfully used in N–to–C-directed one-pot/sequential native chemical ligation using an N-sulfanylethylanilide peptide to give a 64-residue peptide toxin. |
|
言語 |
en |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
thioester |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
S-cyanylation |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
hydrazinolysis |
| キーワード |
|
|
言語 |
en |
|
主題Scheme |
Other |
|
主題 |
native chemical ligation |
| 書誌情報 |
en : Biopolymers(Peptide Science)
巻 106,
号 4,
p. 531-546,
発行日 2015-10-26
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| 収録物ID |
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収録物識別子タイプ |
ISSN |
|
収録物識別子 |
10970282 |
| 収録物ID |
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|
収録物識別子タイプ |
NCID |
|
収録物識別子 |
AA11616617 |
| 収録物ID |
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|
収録物識別子タイプ |
NCID |
|
収録物識別子 |
AA00566142 |
| 出版者 |
|
|
出版者 |
Wiley Periodicals, Inc. |
|
言語 |
en |
| 備考 |
|
|
言語 |
ja |
|
値 |
This is the peer reviewed version of the following article: Miyajima, R. , Tsuda, Y. , Inokuma, T. , Shigenaga, A. , Imanishi, M. , Futaki, S. and Otaka, A. (2016), Preparation of peptide thioesters from naturally occurring sequences using reaction sequence consisting of regioselective S‐cyanylation and hydrazinolysis. Biopolymers, 106: 531-546. doi:10.1002/bip.22757, which has been published in final form at https://doi.org/10.1002/bip.22757. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. |
| EID |
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|
識別子 |
305107 |
|
識別子タイプ |
URI |
| 言語 |
|
|
言語 |
eng |
biopolymers_106_4_531.pdf (1.5 MB)
