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Title: Production of (R)-mandelic acid from styrene, L-phenylalanine, glycerol, or glucose via cascade biotransformations
Authors: Lukito, Benedict Ryan 
Wang, Zilong 
Sundara Sekar, Balaji 
Li, Zhi 
Keywords: Biotransformation
Cascade reaction
Coupled-cells biotransformation
Mandelic acid
Renewable feedstocks
Sustainable synthesis
Issue Date: 4-Mar-2021
Publisher: Springer Science and Business Media Deutschland GmbH
Citation: Lukito, Benedict Ryan, Wang, Zilong, Sundara Sekar, Balaji, Li, Zhi (2021-03-04). Production of (R)-mandelic acid from styrene, L-phenylalanine, glycerol, or glucose via cascade biotransformations. Bioresources and Bioprocessing 8 (1) : 22. ScholarBank@NUS Repository.
Rights: Attribution 4.0 International
Abstract: (R)-mandelic acid is an industrially important chemical, especially used for producing antibiotics. Its chemical synthesis often uses highly toxic cyanide to produce its racemic form, followed by kinetic resolution with 50% maximum yield. Here we report a green and sustainable biocatalytic method for producing (R)-mandelic acid from easily available styrene, biobased L-phenylalanine, and renewable feedstocks such as glycerol and glucose, respectively. An epoxidation-hydrolysis-double oxidation artificial enzyme cascade was developed to produce (R)-mandelic acid at 1.52 g/L from styrene with > 99% ee. Incorporation of deamination and decarboxylation into the above cascade enables direct conversion of L-phenylalanine to (R)-mandelic acid at 913 mg/L and > 99% ee. Expressing the five-enzyme cascade in an L-phenylalanine-overproducing E. coli NST74 strain led to the direct synthesis of (R)-mandelic acid from glycerol or glucose, affording 228 or 152 mg/L product via fermentation. Moreover, coupling of E. coli cells expressing L-phenylalanine biosynthesis pathway with E. coli cells expressing the artificial enzyme cascade enabled the production of 760 or 455 mg/L (R)-mandelic acid from glycerol or glucose. These simple, safe, and green methods show great potential in producing (R)-mandelic acid from renewable feedstocks.[Figure not available: see fulltext.] © 2021, The Author(s).
Source Title: Bioresources and Bioprocessing
ISSN: 2197-4365
DOI: 10.1186/s40643-021-00374-6
Rights: Attribution 4.0 International
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