A BIOLOGICAL APPROACH TO THE SYNTHESIS OF META-HYDROXY PHENYLACETYLENE FROM PHENYLACETYLENE

ACETYLENE-TERMINATED RESINS ARE ONE OF SEVERAL CANDIDATE POLYMERIC MATERIALS BEING DEVELOPED FOR POTENTIAL AEROSPACE APPLICATIONS. THE ACETYLENE-TERMINATED RESINS POSSESS PROPERTIES REQUIRED FOR THE PROPOSED APPLICATIONS SUCH AS TEMPERATURE, MOISTURE, AND SHEAR INSENSITIVITY. THE LIMITING FACTOR FOR THE COMMERCIAL MANUFACTURE OF THESE RESINS IN A COST-EFFECTIVE METHOD FOR THE SYNTHESIS OF AN ESSENTIAL CONSTITUENT, META-HYDROXY PHENYLACETYLENE. CHEMICAL APPROACHES TO THE SYNTHESIS OF META-HYDROXY PHENYLACETYLENE HAVE NOT RESULTED IN AN INEXPENSIVE PRODUCT OF ACCEPTABLE QUALITY. THE PHASE I RESEARCH PROGRAM OUTLINED IN THIS PROPOSAL TAKES A BIOLOGICAL APPROACHE TO THE PROBLEM. TWO POSSIBLE BIOLOGICAL ROUTES EXIST. ONE IS AN ENZYMATIC APPROACH. THE PROPOSED RESEARCH PROGRAM WILL SCREEN COMMERCIALLY AVAILABLE ENZYMES FOR THE ABILITY TO SELECTIVELY HYDROXYLATE PHENYLACETYLENE IN THE META POSITION. THE REACTION CONDITIONS FOR THE SELECTED ENZYME SYSTEMS WILL BE OPTIMIZED. THERE IS PRECEDENCE IN THE LITERATURE FOR THE SELECTIVE ENZYMATIC HYDROXYLATION OF AROMATIC COMPOUNDS. THE SECOND BIOLOGICAL APPROACH IS A MICROBIOLOGICAL CONVERSION. A VARIETY OF MICROORGANISMS WILL BE SCREENED FOR THE ABILITY TO SELECTIVELY HYDROXYLATE PHENYLACETYLENE. THERE ARE NUMEROUS EXAMPLES IN THE LITERATURE OF MICROBIAL HYDROXYLATIONS OF SUBSTITUTED AROMATIC COMPOUNDS. THE GOAL OF THIS PROPOSED RESEARCH PROGRAM IS TO DETERMINE WHICH OF THESE TWO BIOLOGICAL APPROACHES WARRANT FURTHER DEVELOPMENT BASED ON ECONOMIC AND TECHNICALDATA.