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.
Keywords:
antifungal activity; azole; enantioseparation; kinetic resolution; lipase.
© 2014 Wiley Periodicals, Inc.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Acetates / chemistry
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Antifungal Agents / chemistry
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Antifungal Agents / pharmacology*
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Butanols / chemical synthesis
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Butanols / chemistry*
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Butanols / pharmacology
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Drug Evaluation, Preclinical / methods
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Enzymes, Immobilized
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Esters / chemistry*
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Fungal Proteins
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Hydrolysis
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Inhibitory Concentration 50
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Lipase / chemistry*
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Magnetic Resonance Spectroscopy
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Microbial Sensitivity Tests
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Propanols / chemical synthesis
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Propanols / chemistry*
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Propanols / pharmacology
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Stereoisomerism
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Structure-Activity Relationship
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Tetrazoles / chemical synthesis
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Tetrazoles / chemistry*
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Tetrazoles / pharmacology
Substances
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4-(5-(4-chlorophenyl)-2H-tetrazol-2-yl)butan-2-ol
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Acetates
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Antifungal Agents
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Butanols
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Enzymes, Immobilized
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Esters
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Fungal Proteins
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Propanols
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Tetrazoles
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1H-tetrazole
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Novozyme 435
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Lipase