Process for the enantioselective reduction and oxidation, respectively, of steroids
AssigneeIep GmbH
InventorsAntje Gupta, Anke Tschentscher, Maria Bobkova
Life of this patent
Estimating the term…
Abstract
A process for the enantioselective reduction of compounds having a steroid structure (ABCD) including one or several heteroatoms, one or several double bonds and/or aromatic components in the ring structure and having at least one oxo group at positions 3, 7, 11, 12 or 17 in the steroid ring system or in the a-position of any carbon moiety of the steroid structure: comprising providing the oxosteroid compound in the reaction at a concentration of ≧50 g/L, a reduced cofactor NADH or NADPH, a hydroxysteroid dehydrogenase and a secondary alcohol or cycloalknaol to effect the enantioselective reduction.
Claims21
A process for the enantioselective enzymatic reduction of an oxosteroid compound to a hydroxysteroid compound, the process comprising:
- providing an oxosteroid compound having the following steroid structure (ABCD),
- wherein the ring of the steroid structure (ABCD) includes one or several heteroatoms, one or several double bonds and/or one aromatic component and has at least one oxo group at positions 3, 7, 11, 12 or 17 in the steroid structure or in the α-position at any carbon moiety attached to the steroid structure,
- reducing the oxosteroid compound with a hydroxysteroid dehydrogenase in the presence of a cofactor NADH or NADPH, characterized in that:
- (a) the oxosteroid compound is provided in the reaction at a concentration of 50 g/L,
- (b) the oxidized cofactor NAD or NADP formed by the hydroxysteroid dehydrogenase is regenerated continuously by oxidation of a secondary alcohol of formula RXRYCHOH, wherein RX, RY, independently represent a branched or unbranched C1-C8-alkyl and Ctotal≧3, or by oxidation of a C4-C6 cycloalkanol, and
- c) an additional oxidoreductase/alcohol dehydrogenase is used for the oxidation of the secondary alcohol of formula RxRyCHOH or of the cycloalkanol, respectively.
A process for the enzymatic oxidation of a hydroxysteroid compound to an oxosteroid compound, the process comprising:
- providing a hydroxysteroid compound having the following steroid structure (ABCD),
- wherein the ring of the steroid structure (ABCD) includes one or several heteroatoms, one or several double bonds and/or one aromatic component and has at least one hydroxy group at positions 3, 7, 11, 12 or 17 in the steroid structure or in the α-position at any carbon moiety attached to the steroid structure,
- oxidizing the hydroxysteroid compound with a hydroxysteroid dehydrogenase in the presence of a cofactor NAD or NADP, characterized in that:
- (a) the hydroxysteroid compound is provided in the reaction at a concentration of ≧50 g/L,
- (b) the reduced cofactor NADH or NADPH formed by the hydroxysteroid dehydrogenase is regenerated continuously by reduction of a keto compound of formula RXRYCO, wherein RX, RY, independently represent a branched or unbranched C1-C8-alkyl and Ctotal≧3, or by reduction of a C4-C6 cycloalkanone, and
- (c) an additional oxidoreductase/alcohol dehydrogenase is used for the reduction of the keto compound of formula RxRyCO or of the cycloalkanone, respectively.
Dependencies are inferred from the claim text.