Helvetica Chimica Acta p. 1506 - 1520 (1998)
Update date:2022-08-05
Topics:
Wagenknecht, Hans-Achim
Claude, Cécile
Woggon, Wolf-Dietrich
The heme-thiolate protein chloroperoxidase (CPO) catalyzes the chlorination of activated C-H bonds. A reaction mechanism is proposed for this enzymatic transformation (Scheme 1), and a new iron(III) porphyrinate complex 13 is synthesized containing pentafluorophenyl groups at two meso-positions and a thiophenolato ligand coordinating to the Fe-atom (Schemes 2 and 3). Due to the presence of the electron-withdrawing substituents, the catalyst 13 is appreciably resistant to oxidants (HOCl) and chlorinates, e.g., monochlorodimedone (5), with turnover numbers up to 1530. The redox potential of 13, E0 = - 134 mV, and the Soret band (λmax 448 nm) of the CO adduct of the reduced state of 13 are close to the corresponding values of the enzyme CPO.
View MoreMS( MAOSHENG )Chemical CO.,LTD
Contact:+86-519-82726678.82726378
Address:TAOXI INDUSTRY ZONE JINTAN
Zhejiang Newfine Industry Co.,Ltd.
Contact:+86-573-82262042
Address:No.225,Dongqing Road, garoms@163.com
Contact:86-10-62983737; +86-10-51287608
Address:4/F Building C, 2 Shangdi Xinxi Road
Yueyang Hudex Pharmaceuticals Ltd.
Contact:0730-8748800
Address:Wujiang Bridge,Yueyang Economy & Technology Development Zone
Contact:86+21-56421993
Address:3F,BUILDING 10,NO.2889 JINKE ROAD, SHANGHAI.
Doi:10.1039/b005419o
(2000)Doi:10.1002/cjoc.201400684
(2015)Doi:10.1021/jo01017a013
(1965)Doi:10.1002/anie.201306181
(2013)Doi:10.1016/S0040-4020(01)82633-8
(1969)Doi:10.1021/jo981013m
(1998)