The application of toluene dioxygenase in the synthesis of acetylene-terminated resins

Michael G. Williams, Patricia E. Olson, Kestutis J. Tautvydas, Rex M. Bitner, Roger A. Mader, Lawrence P Wackett

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A biotransformation procedure has been developed to prepare intermediates for the synthesis of 3-hydroxyphenylacetylene (3-HPA), a high-value specialty chemical used in the manufacture of acetylene-terminated resins. Pseudomonas putida F39/D containing toluene dioxygenase was used to oxidize a series of substituted benzenes to their respective cis-2,3-dihydroxydihydrobenzene(cis-dihydrodiol) derivatives which in turn could be converted to 3-HPA via a meta-phenol intermediate obtained by acid-catalyzed dehydration. The cis-dihydrodiols derived from the oxidation of phenylacetylene, styrene, acetophenone, and bromobenzene dehydrated to yield predominantly ortho-phenols. Three different phenyl-1,3-dioxolanes were oxidized by P. putida F39/D to three previously undescribed cis-dihydrodiols. Unlike mono-substituted cis-dihydrodiols, phenyl-1,3-dioxolane cis-dihydrodiols were dehydrated to form meta-phenols exclusively. The dehydration products, 3-hydroxyacetophenone and 3-hydroxybenzaldehyde, are suitable precursors for the chemical synthesis of 3-HPA.

Original languageEnglish (US)
Pages (from-to)316-321
Number of pages6
JournalApplied Microbiology and Biotechnology
Volume34
Issue number3
DOIs
StatePublished - Dec 1990

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