Hydrogen bonding modulates the selectivity of enzymatic oxidation by P450: Chameleon oxidant behavior by compound I

Samuël P. De Visser; François Ogliaro; Pankaz K. Sharma; Sason Shaik

doi:10.1002/1521-3773(20020603)41:11<1947::AID-ANIE1947>3.0.CO;2-W

Hydrogen bonding modulates the selectivity of enzymatic oxidation by P450: Chameleon oxidant behavior by compound I

Samuël P. De Visser
, François Ogliaro
, Pankaz K. Sharma
, Sason Shaik^*

^*Corresponding author for this work

Institute of Chemistry

Research output: Contribution to journal › Article › peer-review

118 Scopus citations

Abstract

Changes of two orders of magnitude or more in the epoxidation to hydroxylation ratio of propene by the iron-oxo species 1, the primary active species of cytochrome P450 (see scheme) occur when the molecular species is subject to NH ··· S hydrogen bonding and electronic polarization as in the protein pocket.

Original language	English
Pages (from-to)	1947-1951
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	41
Issue number	11
DOIs	https://doi.org/10.1002/1521-3773(20020603)41:11<1947::AID-ANIE1947>3.0.CO;2-W
State	Published - 3 Jun 2002

Keywords

Density functional calculations
Enzyme catalysis
Epoxidation
Hydroxylation
Solvent effects

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10.1002/1521-3773(20020603)41:11<1947::AID-ANIE1947>3.0.CO;2-W

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title = "Hydrogen bonding modulates the selectivity of enzymatic oxidation by P450: Chameleon oxidant behavior by compound I",

abstract = "Changes of two orders of magnitude or more in the epoxidation to hydroxylation ratio of propene by the iron-oxo species 1, the primary active species of cytochrome P450 (see scheme) occur when the molecular species is subject to NH ··· S hydrogen bonding and electronic polarization as in the protein pocket.",

keywords = "Density functional calculations, Enzyme catalysis, Epoxidation, Hydroxylation, Solvent effects",

author = "\{De Visser\}, \{Samu{\"e}l P.\} and Fran{\c c}ois Ogliaro and Sharma, \{Pankaz K.\} and Sason Shaik",

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doi = "10.1002/1521-3773(20020603)41:11<1947::AID-ANIE1947>3.0.CO;2-W",

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T2 - Chameleon oxidant behavior by compound I

AU - De Visser, Samuël P.

AU - Ogliaro, François

AU - Sharma, Pankaz K.

AU - Shaik, Sason

PY - 2002/6/3

Y1 - 2002/6/3

N2 - Changes of two orders of magnitude or more in the epoxidation to hydroxylation ratio of propene by the iron-oxo species 1, the primary active species of cytochrome P450 (see scheme) occur when the molecular species is subject to NH ··· S hydrogen bonding and electronic polarization as in the protein pocket.

AB - Changes of two orders of magnitude or more in the epoxidation to hydroxylation ratio of propene by the iron-oxo species 1, the primary active species of cytochrome P450 (see scheme) occur when the molecular species is subject to NH ··· S hydrogen bonding and electronic polarization as in the protein pocket.

KW - Density functional calculations

KW - Enzyme catalysis

KW - Epoxidation

KW - Hydroxylation

KW - Solvent effects

UR - https://www.scopus.com/pages/publications/0037014038

U2 - 10.1002/1521-3773(20020603)41:11<1947::AID-ANIE1947>3.0.CO;2-W

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C2 - 19750642

AN - SCOPUS:0037014038

SN - 1433-7851

VL - 41

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EP - 1951

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 11

ER -

Hydrogen bonding modulates the selectivity of enzymatic oxidation by P450: Chameleon oxidant behavior by compound I

Abstract

Keywords

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