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Highly Enantioselective Synthesis of Arylaliphatic Tertiary Alcohols using Mutants of an Esterase from Bacillus subtilis
Author(s) -
Kourist Robert,
Bartsch Sebastian,
Bornscheuer Uwe T.
Publication year - 2007
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200600641
Subject(s) - chemistry , bacillus subtilis , enantioselective synthesis , kinetic resolution , esterase , mutant , substrate (aquarium) , stereochemistry , thiophene , organic chemistry , enzyme , catalysis , biochemistry , bacteria , genetics , oceanography , geology , gene , biology
The kinetic resolution of a series of acetates of arylaliphatic tertiary alcohols was studied using recombinant esterase variants from Bacillus subtilis (BS2) expressed in E. coli . Highest enantioselectivities (E>100) were achieved in the synthesis of 1,1,1‐trifluoro‐2‐phenylbut‐3‐yn‐2‐ol and three para ‐substituted analogues using BS2 mutant G105A. With mutant E188D only two compounds were converted with E>100. For a thiophene analogue or compounds with small variations in the aliphatic chain substantially lower conversions and/or enantioselectivity were observed, which also varied with the BS2 variant used. Thus, small changes in the substrate structure and point mutations in the esterase had a remarkable influence on both activity and enantioselectivity.