Please use this identifier to cite or link to this item:
|Title:||Engineering of P450pyr hydroxylase for the highly regio- and enantioselective subterminal hydroxylation of alkanes|
|Citation:||Yang, Y., Liu, J., Li, Z. (2014-03-17). Engineering of P450pyr hydroxylase for the highly regio- and enantioselective subterminal hydroxylation of alkanes. Angewandte Chemie - International Edition 53 (12) : 3120-3124. ScholarBank@NUS Repository. https://doi.org/10.1002/anie.201311091|
|Abstract:||Terminal-selective cytochrome P450pyr has been successfully engineered through directed evolution for the subterminal hydroxylation of alkanes with excellent regio- and enantioselectivity. A sensitive colorimetric high-throughput screening (HTS) assay was developed for the measurement of both the regioselectivity and the enantioselectivity of a hydroxylation reaction. By using the HTS assay and iterative saturation mutagenesis, sextuple-mutant P450pyrSM1 was created for the hydroxylation of n-octane (1) to give (S)-2-octanol (2) with 98 % ee and >99 % subterminal selectivity. The engineered P450 is the first enzyme for this type of highly selective alkane hydroxylation, being useful for the Ci-H activation and functionalization of alkanes and the preparation of enantiopure alcohols. Molecular modeling provided structure-based understanding of the fully altered regioselectivity and the excellent enantioselectivity. Another sextuple-mutant P450pyrSM2 catalyzed the hydroxylation of propylbenzene (3) to afford (S)-1-phenyl-2-propanol (4) with 95 % ee and 98 % subterminal selectivity. Get a handle on it: Highly regio- and enantioselective subterminal hydroxylation of n-octane and propylbenzene was observed with P450 enzymes obtained by the directed evolution of terminal-selective P450pyr hydroxylase (see scheme). The engineered enzymes with their fully altered selectivities are useful for the functionalization of alkanes and the preparation of enantiomerically pure alcohols. © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.|
|Source Title:||Angewandte Chemie - International Edition|
|Appears in Collections:||Staff Publications|
Show full item record
Files in This Item:
There are no files associated with this item.
checked on Jun 17, 2018
WEB OF SCIENCETM
checked on Jun 4, 2018
checked on Mar 12, 2018
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.