Biocatalytic Enantio-Convergent Preparation of sec-Alcohols using Sulfatases

• Published in: Engineering in life sciences Vol. 4; no. 6; pp. 512 - 516
• Main Authors: Wallner, S.R., Pogorevc, M., Trauthwein, H., Faber, K.
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.12.2004; WILEY‐VCH Verlag
• Subjects: Alcohols; Biocatalysis; Enzymatic processes; Rhodococcus
• ISSN: 1618-0240; 1618-2863
• DOI: 10.1002/elsc.200402151

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. The deracemization of sec‐alcohols via enantioconvergent processes is an elegant possibility to overcome the limitations of 50 % yield kinetic resolution. The deracemization of alcohols can be achieved by using biocatalysts and subsequent chemical reactions. In particular, sulfatases, which work under inversion of configuration, have opened a new approach for the deracemization of alcohols. In this minireview recent developments in enantioconvergent processes are presented, with especial focus on sulfatases.