Production of 6-phenylacetylene picolinic acid from diphenylacetylene by a toluene-degrading Acinetobacter strain.
نویسندگان
چکیده
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.
منابع مشابه
Thermally reactive phenylethynyl-terminated bis(benzylester) and bis(amide) monomers based on semi-enzymatically produced 6-phenylethynyl picolinic acid
The synthesis and isolation of 6-phenylethynyl picolinic acid (PEPCA; IUPAC name: 6-(2-phenylethynyl)pyridine-2-carboxylic acid) was first demonstrated when Acinetobacter sp. strain F4 was used to biotransform diphenylacetylene to the ring-fission product that underwent facile ring closure to form PEPCA in the presence of ammonium ions. Here, the structure and properties of PEPCA were confirmed...
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ورودعنوان ژورنال:
- Applied and environmental microbiology
دوره 69 7 شماره
صفحات -
تاریخ انتشار 2003