Rhodotorula glutinis Phenylalanine/Tyrosine Ammonia Lyase Enzyme Catalyzed Synthesis of the Methyl Ester of para-Hydroxycinnamic Acid and its Potential Antibacterial Activity

Marybeth C MacDonald; Pugazhendhi Arivalagan; Douglas E Barre; Judith A MacInnis; Godwin B D'Cunha

doi:10.3389/fmicb.2016.00281

Rhodotorula glutinis Phenylalanine/Tyrosine Ammonia Lyase Enzyme Catalyzed Synthesis of the Methyl Ester of para-Hydroxycinnamic Acid and its Potential Antibacterial Activity

Front Microbiol. 2016 Mar 8:7:281. doi: 10.3389/fmicb.2016.00281. eCollection 2016.

Authors

Marybeth C MacDonald¹, Pugazhendhi Arivalagan², Douglas E Barre³, Judith A MacInnis¹, Godwin B D'Cunha¹

Affiliations

¹ Department of Chemistry, Cape Breton University Sydney, NS, Canada.
² Department of Environmental Biotechnology, School of Environmental Sciences, Bharathidasan University Tiruchirappalli, India.
³ Department of Health Sciences and Emergency Management, Cape Breton University Sydney, NS, Canada.

Abstract

Biotransformation of L-tyrosine methyl ester (L-TM) to the methyl ester of para- hydroxycinnamic acid (p-HCAM) using Rhodotorula glutinis yeast phenylalanine/tyrosine ammonia lyase (PTAL; EC 4.3.1.26) enzyme was successfully demonstrated for the first time; progress of the reaction was followed by spectrophotometric determination at 315 nm. The following conditions were optimized for maximal formation of p-HCAM: pH (8.5), temperature (37°C), speed of agitation (50 rpm), enzyme concentration (0.080 μM), and substrate concentration (0.50 mM). Under these conditions, the yield of the reaction was ∼15% in 1 h incubation period and ∼63% after an overnight (∼18 h) incubation period. The product (p-HCAM) of the reaction of PTAL with L-TM was confirmed using Nuclear Magnetic Resonance spectroscopy (NMR). Fourier Transform Infra-Red spectroscopy (FTIR) was carried out to rule out potential hydrolysis of p-HCAM during overnight incubation. Potential antibacterial activity of p-HCAM was tested against several strains of Gram-positive and Gram-negative bacteria. This study describes a synthetically useful transformation, and could have future clinical and industrial applications.

Keywords: Rhodotorula glutinis; antibacterial activity; enzyme catalysis; methyl ester of para-hydroxycinnamic acid; phenylalanine/tyrosine ammonia lyase.