Open AccessBiocatalytic Enantio‐Convergent Preparation of sec ‐Alcohols using Sulfatases
Author(s) -
Wallner S.R.,
Pogorevc M.,
Trauthwein H.,
Faber K.
Publication year - 2004
Publication title -
engineering in life sciences
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.547
H-Index - 57
eISSN - 1618-2863
pISSN - 1618-0240
DOI - 10.1002/elsc.200402151
Subject(s) - chemistry , kinetic resolution , enantiomer , hydrolysis , alkyl , enantioselective synthesis , biocatalysis , walden inversion , lipase , yield (engineering) , organic chemistry , stereochemistry , catalysis , combinatorial chemistry , enzyme , reaction mechanism , materials science , metallurgy
The deracemization of sec ‐alcohols via enantioconvergent processes is of high interest in order to overcome the 50 % yield limitations of kinetic resolution. As enantioconvergent processes are characterized by two reactions with one crossing the plane of symmetry, one of these reactions has to proceed with inversion of configuration. In lipase catalyzed resolutions the enzymatic step proceeds with retention of configuration, and the remaining enantiomer is converted by the Mitsunobu reaction or activated esters under inversion of configuration to achieve complete deracemization. In contrast, alkyl sulfatases, which catalyze the enantioselective hydrolysis of sulfate esters, are one of the rare hydrolytic enzymes which work under inversion of configuration. In this minireview we give an overview of the state of the art in enantioconvergent processes for the deracemization of sec ‐alcohols, with the focus on recently developed alkyl‐sulfatases from Rhodococcus spp.