Enantiogroup-differentiating biocatalytic reductions of prochiral Cs -symmetrical dicarbonyl compounds to meso compounds.
The stereoselective reduction of symmetrical prochiral dicarbonyl compounds bearing enantiotopic carbonyl groups yields several stereogenic centers in one step. In a proof-of-concept study, a new approach is described for the enzymatic desymmetrization of 5-nitrononane-2,8-dione via sequential biocatalytic reduction steps utilizing ketoreductases to yield all possible diastereomers of 5-nitrononane-2,8-diol.
Karlsruhe Institute of Technology (KIT), Institute for Biological Interfaces (IBG 1), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany), Fax: (+49) 721-608-2-5546.
Marc
M
Skoupi
Freie Universität Berlin, Department of Biology, Chemistry and Pharmacy, Institute of Chemistry and Biochemistry, Organic Chemistry, Takustr. 3, 14195 Berlin (Germany), Fax: (+49)30-838-460182.
Carine
C
Vaxelaire
TU Dortmund University, Department of Chemistry and Chemical Biology, Inorganic Chemistry, Otto-Hahn-Str. 6, 44227 Dortmund (Germany).
Carsten
C
Strohmann
Freie Universität Berlin, Department of Biology, Chemistry and Pharmacy, Institute of Chemistry and Biochemistry, Organic Chemistry, Takustr. 3, 14195 Berlin (Germany), Fax: (+49)30-838-460182. mathias.christmann@fu-berlin.de.
Mathias
M
Christmann
Karlsruhe Institute of Technology (KIT), Institute for Biological Interfaces (IBG 1), Hermann-von-Helmholtz-Platz 1, 76344 Eggenstein-Leopoldshafen (Germany), Fax: (+49) 721-608-2-5546. niemeyer@kit.edu.
Christof M
CM
Niemeyer
D000438:Alcohols / Q000737:chemistry*; D055162:Biocatalysis; D007659:Ketones / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
D000438:Alcohols; D007659:Ketones
biocatalysis; carbonyl compounds; meso compounds; reduction; stereoselective synthesis