Lipases catalyzed enantioselective hydrolysis of (R,S)-methyl 1,4-benzodioxan-2-carboxylate intermediate for (S)-doxazosin mesylate

• Published in: World journal of microbiology & biotechnology Vol. 24; no. 4; pp. 577 - 579
• Main Authors: Varma, Rita, Kasture, Sangita M, Nene, Sanjay, Kalkote, Uttam R
• Format: Journal Article
• Language: English
• Published: Dordrecht Dordrecht : Springer Netherlands 01.04.2008; Springer Netherlands; Springer; Springer Nature B.V
• Subjects: 1,4-Benzodioxan-2-carboxylate; 1,4-Benzodioxan-2-carboxylic acid; Acids; Alcaligenes; Antihypertensives; Applied Microbiology; Biochemistry; Biological and medical sciences; Biomedical and Life Sciences; Biotechnology; Carboxylic acids; Doxazosin; enantiomers; Environmental Engineering/Biotechnology; Enzymes; Fundamental and applied biological sciences. Psychology; Laboratories; Life Sciences; Lipases; Microbiology; Organic chemicals; Organic chemistry; Original Paper; Potassium; Studies; Yeast; Yeasts; Doxazosin; 1,4-Benzodioxan-2-carboxylate; Enantioselectivity; 1,4-Benzodioxan-2-carboxylic acid; Lipases; Hydrolysis; Enzyme; Carboxylic acid; l,4-Benzodioxan-2-carboxylic acid; Triacylglycerol lipase; Hydrolases; Esterases; Carboxylic ester hydrolases
• ISSN: 0959-3993; 1573-0972
• DOI: 10.1007/s11274-007-9504-6

(S)-1,4-benzodioxan-2-carboxylic acid-1 is used as starting compound for the production of the more effective (S) enantiomer of the drug doxazosin mesylate. The catalytic ability of some commercial lipases for preparations of (S) enantiomer of 1 from (±) methyl 1,4-benzodioxin-2-carboxylate-2 is reported. Lipases from bacterial sources were more successful in resolving the ester than those from the yeast lipases. About 85% enantiomerically pure ester was achieved by lipase from alcaligenes sp.