Effects of introduction of α-carboxylate, N-methyl, and N-formyl groups on intramolecular cyclization of o-quinone amines: Density functional theory-based study

Ryo Kishida, Adhitya Gandaryus Saputro, Ryan Lacdao Arevalo, Hideaki Kasai

研究成果: Contribution to journalArticle査読

4 被引用数 (Scopus)

抄録

o-Quinone amines, which are relevant to various biological processes, can undergo spontaneous intramolecular cyclization (ring closure reaction by amino-terminated hydrocarbon side chain) that deactivates them toward another possible reactions, that is, thiol binding. Density functional theory-based calculation is employed for obtaining the potential energy curves along the CN bond formation in the intramolecular cyclization of various o-quinone amines, viz., dopaminequinone, dopaquinone, N-methyl-dopaminequinone, N-formyl-dopaminequinone, and the corresponding methylene-inserted analogues. The activation barrier is decreased by introduction of α-carboxylate and N-methyl group whereas increased by introduction of N-formyl group. A negative correlation between the activation barriers and the level of highest occupied molecular orbital is pointed out. Furthermore, the methylene-inserted analogues show decreased activation barriers. This is explained by reduction of steric repulsion in the transition state.

本文言語英語
論文番号e25445
ジャーナルInternational Journal of Quantum Chemistry
117
23
DOI
出版ステータス出版済み - 12 5 2017
外部発表はい

All Science Journal Classification (ASJC) codes

  • 原子分子物理学および光学
  • 凝縮系物理学
  • 物理化学および理論化学

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