Enzymatic hydrolysis of esters containing a tetrazole ring

Chirality. 2014 Dec;26(12):811-6. doi: 10.1002/chir.22360. Epub 2014 Jul 28.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acetates / chemistry
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Butanols / chemical synthesis
  • Butanols / chemistry*
  • Butanols / pharmacology
  • Drug Evaluation, Preclinical / methods
  • Enzymes, Immobilized
  • Esters / chemistry*
  • Fungal Proteins
  • Hydrolysis
  • Inhibitory Concentration 50
  • Lipase / chemistry*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Propanols / chemical synthesis
  • Propanols / chemistry*
  • Propanols / pharmacology
  • Stereoisomerism
  • Structure-Activity Relationship
  • Tetrazoles / chemical synthesis
  • Tetrazoles / chemistry*
  • Tetrazoles / pharmacology

Substances

  • 4-(5-(4-chlorophenyl)-2H-tetrazol-2-yl)butan-2-ol
  • Acetates
  • Antifungal Agents
  • Butanols
  • Enzymes, Immobilized
  • Esters
  • Fungal Proteins
  • Propanols
  • Tetrazoles
  • 1H-tetrazole
  • Novozyme 435
  • Lipase