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Synthesis of α-hydroxy ketones and vicinal (R, R)-diols by Bacillus clausii DSM 8716ᵀ butanediol dehydrogenase

  • α-hydroxy ketones (HK) and 1,2-diols are important building blocks for fine chemical synthesis. Here, we describe the R-selective 2,3-butanediol dehydrogenase from B. clausii DSM 8716ᵀ (BcBDH) that belongs to the metal-dependent medium chain dehydrogenases/reductases family (MDR) and catalyzes the selective asymmetric reduction of prochiral 1,2-diketones to the corresponding HK and, in some cases, the reduction of the same to the corresponding 1,2-diols. Aliphatic diketones, like 2,3-pentanedione, 2,3-hexanedione, 5-methyl-2,3-hexanedione, 3,4-hexanedione and 2,3-heptanedione are well transformed. In addition, surprisingly alkyl phenyl dicarbonyls, like 2-hydroxy-1-phenylpropan-1-one and phenylglyoxal are accepted, whereas their derivatives with two phenyl groups are not substrates. Supplementation of Mn²⁺ (1 mM) increases BcBDH's activity in biotransformations. Furthermore, the biocatalytic reduction of 5-methyl-2,3-hexanedione to mainly 5-methyl-3-hydroxy-2-hexanone with only small amounts of 5-methyl-2-hydroxy-3-hexanone within an enzyme membrane reactor is demonstrated.

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Author:Lukas Muschallik, Denise MolinnusORCiD, Melanie Jablonski, Carina Ronja Kipp, Johannes Bongaerts, Martina Pohl, Torsten WagnerORCiD, Michael Josef SchöningORCiD, Thorsten Selmer, Petra SiegertORCiD
Parent Title (English):RSC Advances
Publisher:RSC Publishing
Place of publication:London
Document Type:Article
Year of Completion:2020
Date of the Publication (Server):2020/04/03
First Page:12206
Last Page:12216
Institutes:FH Aachen / Fachbereich Chemie und Biotechnologie
FH Aachen / Fachbereich Medizintechnik und Technomathematik
FH Aachen / INB - Institut für Nano- und Biotechnologien
collections:Open Access
Verlag / RSC Publishing
Licence (German):License LogoCreative Commons - Namensnennung