Abstract
Background: l-Phenyllactic acid (l-PLA)—a valuable building block in the pharmaceutical and chemical industry—has recently emerged as an important monomer in the composition of the novel degradable biocompatible material of polyphenyllactic acid. However, both normally chemically synthesized and naturally occurring phenyllactic acid are racemic, and the product yields of reported l-PLA synthesis processes remain unsatisfactory. Methods: We developed a novel recombinant Escherichia coli strain, co-expressing l-lactate dehydrogenase (l-LDH) from Lactobacillus plantarum subsp. plantarum and glucose dehydrogenase (GDH) from Bacillus megaterium, to construct a recombinant oxidation/reduction cycle for whole-cell biotransformation of phenylpyruvic acid (PPA) into chiral l-PLA in an enantioselective and continuous manner. Results: During fed-batch bioconversion with intermittent PPA feeding, l-PLA yield reached 103.8 mM, with an excellent enantiomeric excess of 99.7%. The productivity of l-PLA was as high as 5.2 mM·h−1 per OD600 (optical density at 600 nm) of whole cells. These results demonstrate the efficient production of l-PLA by the one-pot biotransformation system. Therefore, this stereoselective biocatalytic process might be a promising alternative for l-PLA production.
Highlights
The development of novel natural antimicrobial compounds to preserve food and feed has gained importance in recent years due to the increasing demand for chemical preservative-free products by consumers and the increased interest in food biopreservation [1,2]. 3-Phenyllactic acid (2-hydroxy-3-phenylpropanoic acid; PLA)—a special chemical widely used for the synthesis of chiral pharmaceutical and biorefinery chemicals, including bio-based polymers [3]—has been recently identified as a novel natural antiseptic agent with broad-spectrum and effective inhibitory activity against a variety of food-borne microorganisms, including a wide range of bacteria and fungi [4,5,6,7,8]
As a result of a chiral carbon atom in its molecule, PLA occurs as two enantiomers, L-3-phenyllactic acid (L-PLA) and D-3-phenyllactic acid (D-PLA), both of which are valuable chiral building blocks but have different biological functions, leading to their various applications in the pharmaceutical and chemical industries [11]
D -PLA is applied in the synthesis of hypoglycemic drugs and high-efficiency and low-toxicity anthelmintics, while L-PLA is an important precursor for the synthesis of the non-protein
Summary
The development of novel natural antimicrobial compounds to preserve food and feed has gained importance in recent years due to the increasing demand for chemical preservative-free products by consumers and the increased interest in food biopreservation [1,2]. 3-Phenyllactic acid (2-hydroxy-3-phenylpropanoic acid; PLA)—a special chemical widely used for the synthesis of chiral pharmaceutical and biorefinery chemicals, including bio-based polymers [3]—has been recently identified as a novel natural antiseptic agent with broad-spectrum and effective inhibitory activity against a variety of food-borne microorganisms, including a wide range of bacteria and fungi [4,5,6,7,8]. Food and pharmaceutical purposes, chiral monomers with high optical purity and low impurity levels important precursor the synthesis of the non-protein amino acid statine, drugs, are aan prerequisite to avoid for toxicosis and isomeric ballast [15]. Purposes, chiral monomers with high optical purity and low impurity levels are a prerequisite to Various approaches for preparing PLA have been developed in recent years, including traditional avoid toxicosis and isomeric ballast [15]. SynthesisVarious methods, chiral isomers have been produced with high yields and high conversion approaches for preparing PLA have been developed in recent years, including traditional rates,chemical but at methods, the expense of the environment and methods extreme[16,17,18,19,20].
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