Journal of Organic Chemistry p. 2902 - 2906 (1986)
Update date:2022-08-11
Topics:
Riva, Sergio
Bovara, Roberto
Pasta, Piero
Carrea, Giacomo
NAD(P)-dependent hydroxysteroid dehydrogenases were used as catalysts for the oxidoreduction of the hydroxyl-keto groups of cholic acid (3α,7α,12α-trihydroxy-5β-cholan-24-oic acid) and dehydrocholic acid (3,7,12-trioxo-5β-cholan-24-oic acid).Cholic acid was regiospecifically oxidized, on a preparative scale, at each of the three possible positions, and dehydrocholic acid regio- and stereospecifically reduced at each of the three positions.The compounds were quantitatively transformed and the products were 97-99percent pure.The assignment of product structure was made by NMR.The nicotinamide cofactors were enzymatically regenerated, in situ, with the α-ketoglutarate/glutamate dehydrogenase, formate/formate dehydrogenase or glucose/glucose dehydrogenase systems.The enzymes were employed in the free form or immobilized on Sepharose CL-4B.
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