caa a22 4500 465823211 CHVBK 20180323112141.0 cr unu---uuuuu 170327e19901201xx s 000 0 eng 10.1007/BF00170050 doi (NATIONALLICENCE)springer-10.1007/BF00170050 The application of toluene dioxygenase in the synthesis of acetylene-terminated resins [Elektronische Daten] [Michael Williams, Patricia Olson, Kestutis Tautvydas, Rex Bitner, Roger Mader, Lawrence Wackett] Summary: 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. Springer-Verlag, 1990 Williams Michael Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut Olson Patricia Gray Freshwater Biological Institute and Department of Biochemistry, University of Minnesota, 55392, Navarre, MN, USA aut Tautvydas Kestutis Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut Bitner Rex Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut Mader Roger Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut Wackett Lawrence Gray Freshwater Biological Institute and Department of Biochemistry, University of Minnesota, 55392, Navarre, MN, USA aut Applied Microbiology and Biotechnology Springer-Verlag 34/3(1990-12-01), 316-321 0175-7598 34:3<316 1990 34 253 https://doi.org/10.1007/BF00170050 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF00170050 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Williams Michael Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut NATIONALLICENCE 700 1- Olson Patricia Gray Freshwater Biological Institute and Department of Biochemistry, University of Minnesota, 55392, Navarre, MN, USA aut NATIONALLICENCE 700 1- Tautvydas Kestutis Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut NATIONALLICENCE 700 1- Bitner Rex Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut NATIONALLICENCE 700 1- Mader Roger Biotechnology Section, 3M Company, 55144-1000, St. Paul, MN, USA aut NATIONALLICENCE 700 1- Wackett Lawrence Gray Freshwater Biological Institute and Department of Biochemistry, University of Minnesota, 55392, Navarre, MN, USA aut NATIONALLICENCE 773 0- Applied Microbiology and Biotechnology Springer-Verlag 34/3(1990-12-01), 316-321 0175-7598 34:3<316 1990 34 253 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer