Hyperconjugation with lone pair of morpholine nitrogen stabilizes transition state for phenyl hydroxylation in CYP3A4 metabolism of (S)-N-[1-(3-morpholin-4-yl phenyl) ethyl]-3-phenylacrylamide

Abdul Rajjak Shaikh, Ewa Broclawik, Mohamed Ismael, Hideyuki Tsuboi, Michihisa Koyama, Momoji Kubo, Carlos A. Del Carpio, Akira Miyamoto

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

Using quantum chemical modelling we describe a novel effect in the mechanism of CYP3A4 metabolism for the arene substrate with o-substituent yielding a lone pair donation to conjugate π system; this will compensate for the loss of aromaticity on formation of the tetrahedral complex and lower the rate-determining energy barrier.

Original languageEnglish
Pages (from-to)523-527
Number of pages5
JournalChemical Physics Letters
Volume419
Issue number4-6
DOIs
Publication statusPublished - 2006 Feb 26

ASJC Scopus subject areas

  • Physics and Astronomy(all)
  • Physical and Theoretical Chemistry

Fingerprint Dive into the research topics of 'Hyperconjugation with lone pair of morpholine nitrogen stabilizes transition state for phenyl hydroxylation in CYP3A4 metabolism of (S)-N-[1-(3-morpholin-4-yl phenyl) ethyl]-3-phenylacrylamide'. Together they form a unique fingerprint.

  • Cite this