Exploitation of the alcohol dehydrogenase-acetone NADP-regeneration system for the enzymatic preparative-scale production of 12-ketochenodeoxycholic acid.
The performance of a new NADP-regeneration system, based on the use of alcohol dehydrogenase (ADH)-acetone, has been investigated for the regioselective oxidation of cholic acid (1) to 12-ketochenodeoxycholic acid (2). Enzymes stabilities and substrate and/or product inhibitory effects under defined synthetic reaction conditions have been evaluated. The optimized system, based on a 4% w/v solution of 1 in a reaction mixture containing 25% v/v acetone, allowed the preparative scale transformation of 1 into 2 with a 92% conversion.
Fossati
Elena
E
Istituto di Chimica del Riconoscimento Molecolare, C.N.R., Via Mario Bianco 9, 20131 Milano, Italy.
Polentini
Fausto
F
Carrea
Giacomo
G
Riva
Sergio
S
D000096:Acetone / Q000737:chemistry / Q000378:metabolism*; D000429:Alcohol Oxidoreductases / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism*; D001419:Bacteria / Q000201:enzymology; D001709:Biotechnology / Q000379:methods; D002384:Catalysis; D002635:Chenodeoxycholic Acid / Q000031:analogs & derivatives* / Q000096:biosynthesis; D019826:Cholic Acid / Q000737:chemistry / Q000378:metabolism; D004795:Enzyme Stability; D006913:Hydroxysteroid Dehydrogenases / Q000037:antagonists & inhibitors / Q000737:chemistry / Q000378:metabolism; D009249:NADP / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
D002635:Chenodeoxycholic Acid; D000096:Acetone; C025576:3,7-dihydroxy-12-oxocholanoic acid; D009249:NADP; D000429:Alcohol Oxidoreductases; D006913:Hydroxysteroid Dehydrogenases; C019189:12 alpha-hydroxysteroid dehydrogenase; C019642:alcohol dehydrogenase (NADP+); D019826:Cholic Acid