Abstract
AbstractEnantiopure d‐phenylglycine and its derivatives are an important group of chiral amino acids with broad applications in thepharmaceutical industry. However, the existing synthetic methods for d‐phenylglycine mainly rely on toxic cyanide chemistry and multistep processes. To provide green and safe alternatives, we envisaged cascade biocatalysis for the one‐pot synthesis of d‐phenylglycine from racemic mandelic acid, styrene, and biobased l‐phenylalanine, respectively. Recombinant Escherichia coli (LZ110) was engineered to coexpress four enzymes to catalyze a 3‐step reaction in one pot, transforming mandelic acid (210 mM) to give enantiopure d‐phenylglycine in 29.5 g L−1 (195 mM) with 93% conversion. Using the same whole‐cell catalyst, twelve other d‐phenylglycine derivatives were also produced from the corresponding mandelic acid derivatives in high conversion (58–94%) and very high ee (93–99%). E. coli (LZ116) expressing seven enzymes was constructed for the transformation of styrene to enantiopure d‐phenylglycine in 80% conversion via a one‐pot 6‐step cascade biotransformation. Twelve substituted d‐phenylglycines were also produced from the corresponding styrene derivatives in high conversion (45–90%) and very high ee (92–99%) via the same cascade reactions. A nine‐enzymeexpressing E. coli (LZ143) was engineered to transform biobased l‐phenylalanine to enantiopure d‐phenylglycine in 83% conversion via a one‐pot 8‐step transformation. Preparative biotransformations were also demonstrated. The high‐yielding synthetic methods use cheap and green reagents (ammonia, glucose, and/or oxygen), and E. coli whole‐cell catalysts, thus providing green and useful alternative methods for manufacturing d‐phenylglycine.magnified image
Published Version
Talk to us
Join us for a 30 min session where you can share your feedback and ask us any queries you have
Schedule a call