Journal of Organic Chemistry p. 88 - 92 (1988)
Update date:2022-08-12
Topics:
Riva, Sergio
Bovara, Roberto
Zetta, Lucia
Pasta, Piero
Ottolina, Gianluca
Carrera, Giacomo
Enzymatic α/β inversion of the C-3 hydroxyl of numerous bile acids containing different numbers of hydroxyl groups in the skeleton and side chains of different lengths has been carried out.Inversion was obtained in two steps through the sequential use of the commercial enzymes 3α- and 3β-hydroxysteroid dehydrogenase, employed in the free form or immobilized on Eupergit C.The transformations were practically quantitative and the products more than 98percent pure.NAD was regenerated in situ with the pyruvate/lactic dehydrogenase system and NADH with the formate/formate dehydrogenase system.The effects of product inhibition on reaction rates and the favorable effects produced by low concentrations (7-10percent, v/v) of ethyl acetate and ethanol were also examined.
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