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Applied and Environmental Microbiology, July 2003, p. 4037-4042, Vol. 69, No. 7
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.7.4037-4042.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.

Production of 6-Phenylacetylene Picolinic Acid from Diphenylacetylene by a Toluene-Degrading Acinetobacter Strain

Jim C. Spain,1* Shirley F. Nishino,1 Bernard Witholt,2 Loon-Seng Tan,3 and Wouter A. Duetz2,{dagger}

Air Force Research Laboratory, Tyndall Air Force Base, Florida,1 Institute of Biotechnology, ETH Hönggerberg, HPT, CH 8093 Zürich, Switzerland,2 Air Force Research Laboratory, Wright-Patterson Air Force Base, Ohio3

Received 9 September 2002/ Accepted 20 March 2003

Several strategies for using enzymes to catalyze reactions leading to the synthesis of relatively simple substituted picolinic acids have been described. The goal of the work described here was to synthesize a more complex molecule, 6-phenylacetylene picolinic acid [6-(2-phenylethynyl)pyridine-2-carboxylic acid], for use as a potential endcapping agent for aerospace polymers. We screened 139 toluene-degrading strains that use a variety of catabolic pathways for the ability to catalyze oxidative transformation of diphenylacetylene. Acinetobacter sp. strain F4 catalyzed the overall conversion of diphenylacetylene to a yellow metabolite, which was identified as a putative meta ring fission product (2-hydroxy-8-phenyl-6-oxoocta-2,4-dien-7-ynoic acid [RFP]). The activity could be sustained by addition of toluene at a flow rate determined empirically so that the transformations were sustained in spite of the fact that toluene is a competitive inhibitor of the enzymes. The overall rate of transformation was limited by the instability of RFP. The RFP was chemically converted to 6-phenylacetylene picolinic acid by treatment with ammonium hydroxide. The results show the potential for using the normal growth substrate to provide energy and to maintain induction of the enzymes involved in biotransformation during preliminary stages of biocatalyst development.

* Corresponding author. Mailing address: AFRL/MLQL, 139 Barnes Dr., Ste. 2, Tyndall AFB, FL 32403-5323. Phone: (850) 283-6058. Fax: (850) 283-6090. E-mail: jim.spain{at}tyndall.af.mil.

{dagger} Present address: ENZYSCREEN BV, 2333 AL Leiden, The Netherlands.

Applied and Environmental Microbiology, July 2003, p. 4037-4042, Vol. 69, No. 7
0099-2240/03/$08.00+0     DOI: 10.1128/AEM.69.7.4037-4042.2003
Copyright © 2003, American Society for Microbiology. All Rights Reserved.





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