Kinetic resolution of 2-hydroxymethyl-1,4-benzodioxanes by Pseudomonas fluorescens

Krisztina Kónya, Renáta Ferenczi, Andrea Czompa, Attila Kiss-Szikszai, Tibor Kurtán, Sándor Antusa

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6 Citations (Scopus)

Abstract

Pseudomonas fluorescens lipase-catalyzed transesterification of 2-hydroxymethyl-1,4-benzodioxanes of different substitution patterns were studied in the presence of vinyl acetate in organic solvents. The influence of structural features on the conversion and enantioselectivity is discussed and it is shown that the presence of a C-3 methyl or aryl substituent significantly hinders the binding of the substrate to the active site of the enzyme. Thus, with a bulky C-3 substituent no transesterification of the 2-hydroxymethyl group could be observed.

Original languageEnglish
Pages (from-to)200-210
Number of pages11
JournalArkivoc
Volume2008
Issue number3
DOIs
Publication statusPublished - Jul 14 2008

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Keywords

  • 1,4-benzodioxanes
  • Kinetic resolution
  • Pseudomonas fluorescens

ASJC Scopus subject areas

  • Organic Chemistry

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