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EnglishWe report the very efficient biotransformation of cholic acid to 7-keto- and 7,12-diketocholic acids with Acinetobacter calcoaceticus lwoffii. The enzymes responsible of the biotransformation (i.e. 7alfa- and 12alfa-hydroxysteroid dehydrogenases) are partially purified and employed in a new chemo-enzymatic synthesis of ursodeoxycholic acid starting from cholic acid. The first step is the 12alfa-HSDH-mediated total oxidation of sodium cholate followed by the Wolf–Kishner reduction of the carbonyl group to chenodeoxycholic acid. This acid is then quantitatively oxidized with 7alfa-HSDH to 7-ketochenodeoxycholic acid, that was chemically reduced to ursodeoxycholic acid (70% overall yield).
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| Data di pubblicazione: | 2008 | |
| Titolo: | 7α- and 12α-Hydroxysteroid dehydrogenases from Acinetobacter calcoaceticus lwoffii: a new integrated chemo-enzymatic route to ursodeoxycholic acid. | |
| Autori: | P.P. GIOVANNINI; A. GRANDINI; D. PERRONE; P. PEDRINI; G. FANTIN; M. FOGAGNOLO | |
| Rivista: | STEROIDS | |
| Parole Chiave: | 12α-Hydroxysteroid dehydrogenase; 7α-Hydroxysteroid dehydrogenase; Oxidation; Cholic acid; Ursodeoxycholic acid | |
| Abstract: | We report the very efficient biotransformation of cholic acid to 7-keto- and 7,12-diketocholic acids with Acinetobacter calcoaceticus lwoffii. The enzymes responsible of the biotransformation (i.e. 7alfa- and 12alfa-hydroxysteroid dehydrogenases) are partially purified and employed in a new chemo-enzymatic synthesis of ursodeoxycholic acid starting from cholic acid. The first step is the 12alfa-HSDH-mediated total oxidation of sodium cholate followed by the Wolf–Kishner reduction of the carbonyl group to chenodeoxycholic acid. This acid is then quantitatively oxidized with 7alfa-HSDH to 7-ketochenodeoxycholic acid, that was chemically reduced to ursodeoxycholic acid (70% overall yield). | |
| Digital Object Identifier (DOI): | 10.1016/j.steroids.2008.06.013 | |
| Handle: | http://hdl.handle.net/11392/527524 | |
| Appare nelle tipologie: | 03.1 Articolo su rivista |
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