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Frontispiece: Mechanistic Study of the Stereoselective Hydroxylation of [2‐ 2 H 1 ,3‐ 2 H 1 ]Butanes Catalyzed by Cytochrome P450 BM3 Variants
Author(s) -
Yang ChungLing,
Lin ChengHung,
Luo WenI,
Lee TsuLin,
Ramu Ravirala,
Ng Kok Yaoh,
Tsai YiFang,
Wei GuorTzo,
Yu Steve S.F.
Publication year - 2017
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201781163
Subject(s) - butane , hydroxylation , chemistry , kinetic isotope effect , catalysis , deuterium , alkane , stereochemistry , stereoselectivity , cytochrome p450 , substrate (aquarium) , crystallography , enzyme , organic chemistry , physics , oceanography , quantum mechanics , geology
Catalytic mechanism of cytochrome P450 A high H/D kinetic isotope effect (KIE) (18–25) is observed from the hydroxylation of tailored di‐deuterated butane substrate, (2 S ,3 S )‐[2‐ 2 H 1 ,3‐ 2 H 1 ]butane, mediated by engineered cytochrome P450 BM3. For the first time, the experimental evidence that supports the participation of quantum tunneling at the secondary C–H bond oxidized by P450 BM3 is demonstrated. This mechanistic revelation provides the basis for the development of biomimetic iron based catalysts for small alkane oxidation or the process for “gas‐to‐liquid” (GTL) conversion. For more information, see the Full Paper by S. Yu et al. on page 2571 ff.