2006年3月
Enol-to-keto tautomerism of peptide groups
JOURNAL OF PHYSICAL CHEMISTRY B
- ,
- ,
- ,
- 巻
- 110
- 号
- 9
- 開始ページ
- 4443
- 終了ページ
- 4450
- 記述言語
- 英語
- 掲載種別
- DOI
- 10.1021/jp056250p
- 出版者・発行元
- AMER CHEMICAL SOC
Density functional based simulations, performed on polyglycine containing an enol peptide group [-C(OH)N-] which is a structural isomer of a keto form [-CONH-], show that in the enol-to-keto tautomeric reaction, the enol peptide group is less stable than the keto form, and that the enol-to-keto tautomerism is characterized by a cis/trans isomerization of the C-N peptide bond. The rate-limiting step in the cis/trans isomerization is a hydrogen migration from O to N atoms in the peptide group with a transition state consisting of a four-membered ring in the cis configuration. An analysis of the cis/trans isomerization pathway shows that the mechanisms for the cis/trans isomerization are essentially different between the enol and keto forms.
- リンク情報
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- DOI
- https://doi.org/10.1021/jp056250p
- CiNii Articles
- http://ci.nii.ac.jp/naid/80019280605
- PubMed
- https://www.ncbi.nlm.nih.gov/pubmed/16509747
- Web of Science
- https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=JSTA_CEL&SrcApp=J_Gate_JST&DestLinkType=FullRecord&KeyUT=WOS:000235944500087&DestApp=WOS_CPL
- ID情報
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- DOI : 10.1021/jp056250p
- ISSN : 1520-6106
- CiNii Articles ID : 80019280605
- PubMed ID : 16509747
- Web of Science ID : WOS:000235944500087