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Extreme Rate Acceleration by Axial Thiolate Coordination on the Isomerization of Endoperoxide Catalyzed by Iron Porphyrin
Author(s) -
Yamane Takehiro,
Makino Kohei,
Umezawa Naoki,
Kato Nobuki,
Higuchi Tsunehiko
Publication year - 2008
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200800137
Subject(s) - isomerization , porphyrin , chemistry , heme , catalysis , photochemistry , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , enzyme
A coordinated effort : The isomerization mechanism of prostaglandin H 2 (PGH 2 ), which is catalytically isomerized to prostacyclin or thromboxane A 2 by cytochrome P450s, was investigated using a heme‐thiolate complex and an endoperoxide. Isomerization of endoperoxides proceeded very rapidly with this complex, whereas imidazole‐ or chloride‐ligated heme had slight or no catalytic activity (see scheme).