Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 2, Pages 852-862Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c02106
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An efficient preparative-scale synthetic procedure of L-phenylalanine derivatives has been developed using mutant variants of rigorous reaction engineering. The AtPAL-catalyzed hydroamination reaction of cinnamic acids provided several unnatural amino acids of high synthetic value, significantly surpassing the catalytic efficiency of previously reported PcPAL-based biotransformations. The AtPAL variants tolerated high substrate and product concentrations, representing an important extension of the PAL-toolbox, while the engineered biocatalytic procedures of improved E-factor and spacetime yields fulfill the requirements of sustainable and green chemistry, providing facile access to valuable amino acid building blocks.
An efficient preparative-scale synthetic procedure of Lphenylalanine derivatives has been developed using mutant variants of rigorous reaction engineering, the AtPAL-catalyzed hydroamination reaction of cinnamic acids provided several unnatural amino acids of high synthetic value, such as (S)-m- and (S)-p-methoxyphenylalanine; (S)-o- and (S)-mmethylphenylalanine; and (S)-o- and (S)-p-bromophenylalanine at preparative scale, significantly surpassing the catalytic efficiency in terms of conversions and yields of the previously reported PcPAL-based biotransformations. The AtPAL variants tolerated high substrate and product concentrations, representing an important extension of the PAL-toolbox, while the engineered biocatalytic procedures of improved E-factor and spacetime yields fulfill the requirements of sustainable and green chemistry, providing facile access to valuable amino acid building blocks.
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