Document Detail


7alpha- and 12alpha-Hydroxysteroid dehydrogenases from Acinetobacter calcoaceticus lwoffii: a new integrated chemo-enzymatic route to ursodeoxycholic acid.
MedLine Citation:
PMID:  18674553     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
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. 7alpha- and 12alpha-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 12alpha-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 7alpha-HSDH to 7-ketochenodeoxycholic acid, that was chemically reduced to ursodeoxycholic acid (70% overall yield).
Authors:
Pier Paolo Giovannini; Alessandro Grandini; Daniela Perrone; Paola Pedrini; Giancarlo Fantin; Marco Fogagnolo
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Publication Detail:
Type:  Journal Article     Date:  2008-07-12
Journal Detail:
Title:  Steroids     Volume:  73     ISSN:  0039-128X     ISO Abbreviation:  Steroids     Publication Date:  2008 Dec 
Date Detail:
Created Date:  2008-11-17     Completed Date:  2009-04-17     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  0404536     Medline TA:  Steroids     Country:  United States    
Other Details:
Languages:  eng     Pagination:  1385-90     Citation Subset:  IM    
Affiliation:
Dipartimento di Biologia ed Evoluzione, Università di Ferrara, C.so Ercole I d'Este 32, I-44100 Ferrara, Italy.
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MeSH Terms
Descriptor/Qualifier:
Acinetobacter calcoaceticus / enzymology*
Biotransformation
Catalysis
Cells, Cultured
Cholic Acids / metabolism
Hydroxysteroid Dehydrogenases / isolation & purification,  metabolism*
Ursodeoxycholic Acid / metabolism*
Chemical
Reg. No./Substance:
0/Cholic Acids; 128-13-2/Ursodeoxycholic Acid; EC 1.1.-/Hydroxysteroid Dehydrogenases; EC 1.1.1.159/7 alpha-hydroxysteroid dehydrogenase; EC 1.1.1.176/12 alpha-hydroxysteroid dehydrogenase

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine


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