title: Enzymatic hydrolysis of esters containing a tetrazole ring.
abstract: The lipase-catalyzed enantioselective hydrolysis of acetates containing tetrazole moiety was studied. Among all tested lipases, Novozyme SP 435 allowed to obtain optically active 4-(5-aryl-2H-tetrazol-2yl)butan-2-ol and 1-(5-aryl-2H-tetrazol-2yl)-propan-2-ol and their acetates with the highest optical purities (ee = 95%-99%) and excellent enantioselectivity (E>100). Some of the synthesized tetrazole derivatives were screened for their antifungal activity. Racemic mixtures of 4-[5-(4-chlorophenyl)-2H-tetrazol-2-yl)butan-2-ol as well as pure enantiomers of this compound showed promising antifungal activity against F. sambucinum, F. oxysporum, C. coccodes, and A. niger.
authors: Faculty of Chemistry, Institute of Biotechnology, Warsaw University of Technology, Warsaw, Poland.
authors: Edyta
authors: E
authors: Łukowska-Chojnacka
authors: Jolanta
authors: J
authors: Mierzejewska
mesh_terms: D000085:Acetates / Q000737:chemistry; D000935:Antifungal Agents / Q000737:chemistry / Q000494:pharmacology*; D000440:Butanols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D004353:Drug Evaluation, Preclinical / Q000379:methods; D004800:Enzymes, Immobilized; D004952:Esters / Q000737:chemistry*; D005656:Fungal Proteins; D006868:Hydrolysis; D020128:Inhibitory Concentration 50; D008049:Lipase / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D020005:Propanols / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D013777:Tetrazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: C000599984:4-(5-(4-chlorophenyl)-2H-tetrazol-2-yl)butan-2-ol; D000085:Acetates; D000935:Antifungal Agents; D000440:Butanols; D004800:Enzymes, Immobilized; D004952:Esters; D005656:Fungal Proteins; D020005:Propanols; D013777:Tetrazoles; C045574:1H-tetrazole; C093667:Novozyme 435; D008049:Lipase
keywords: antifungal activity; azole; enantioseparation; kinetic resolution; lipase