Biocatalytic enantioconvergent separation of racemic mandelic acid

Choi, Won Jae; Lee, Ki Young; Kang, Sang Hoon; Lee, Sun Bok

doi:10.1016/j.seppur.2006.06.024

Cited by 32 publications

(13 citation statements)

References 10 publications

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“…Kinetic resolution of dl -mandelic acid also could be performed by other biocatalysis processes. However, the processes using lipase or nitrilase resulted in rather low d -mandelic acid concentrations [1-4,29-31]. Enantioselective oxidation of the l -enantiomer from racemic mandelic acid to prepare d -enantiomer is an attractive procedure because it uses inexpensive starting material and has high product yield.…”

Section: Resultsmentioning

confidence: 99%

“…Chemical processes for mandelic acid production result in the racemic mixture of both stereospecific forms. Several biocatalytic methods, including lipase catalyzed enantioselective esterification [4], oxidoreductase catalyzed enantioselective oxidation, and microbial mediated enantioselective degradation [5-10], have been developed to prepare d -mandelic acid from racemic mandelic acid. Among these routes, oxidative resolution of racemic mandelic acid is much more promising because of its easy manipulation, exclusion of co-substrate addition, and high yield.…”

Section: Introductionmentioning

confidence: 99%

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Rationally re-designed mutation of NAD-independent l-lactate dehydrogenase: high optical resolution of racemic mandelic acid by the engineered Escherichia coli

et al. 2012

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BackgroundNAD-independent l-lactate dehydrogenase (l-iLDH) from Pseudomonas stutzeri SDM can potentially be used for the kinetic resolution of small aliphatic 2-hydroxycarboxylic acids. However, this enzyme showed rather low activity towards aromatic 2-hydroxycarboxylic acids.ResultsVal-108 of l-iLDH was changed to Ala by rationally site-directed mutagenesis. The l-iLDH mutant exhibited much higher activity than wide-type l-iLDH towards l-mandelate, an aromatic 2-hydroxycarboxylic acid. Using the engineered Escherichia coli expressing the mutant l-iLDH as a biocatalyst, 40 g·L-1 of dl-mandelic acid was converted to 20.1 g·L-1 of d-mandelic acid (enantiomeric purity higher than 99.5%) and 19.3 g·L-1 of benzoylformic acid.ConclusionsA new biocatalyst with high catalytic efficiency toward an unnatural substrate was constructed by rationally re-design mutagenesis. Two building block intermediates (optically pure d-mandelic acid and benzoylformic acid) were efficiently produced by the one-pot biotransformation system.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Rationally re-designed mutation of NAD-independent l-lactate dehydrogenase: high optical resolution of racemic mandelic acid by the engineered Escherichia coli

et al. 2012

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“…However, the idea to use the TSP-EMR to resolve racemic mixtures was proposed by Matson and co-workers who described the DKR of racemic naproxen ethyl ester 40 and (R, S)-ibuprofen. 41 Choi et al 42 used two enzymes suspended in each phase to carry-out the DKR of racemic mandelic acid as described in Fig. 7.…”

Section: Dynamic Kinetic Resolution Of Racemic Mandelic Acidmentioning

confidence: 99%

Enzymatic membrane reactors: the determining factors in two separate phase operations

Agustian¹,

Kamaruddin²,

Bhatia³

2011

J of Chemical Tech & Biotech

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A two separate phase-enzymatic membrane reactor is an attractive process since it has a large interfacial area and exchange surfaces, simultaneous reaction and separation and other benefits. Many factors influence its successful operation, and these include characteristics of the enzyme, membrane, circulating fluids and reactor operations. Although the operating conditions are the main factor, other factors must be considered before, during or after its application. At the initial stage of reactor development, the solubility of substrates and products, type of operation, membrane material and size, enzyme preparation and loading procedure, and cleanliness of the recirculated fluids should be specified. The immobilization site, reactor arrangement, dissolved or no-solvent operation, classic or emulsion operation and immobilized or suspended enzyme(s) are determined later. Some factors still need further studies. Utilization of the technology is described for use from multigram-to plant-scale capacity to process racemic and achiral compounds. The racemates were resolved primarily by kinetic resolution, but dynamic kinetic resolution has been exploited. The technology focused on hydrolytic reactions, but esterification processes were also exploited.

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“…The DKR of racemic mandelic acid by esterification was recently described by Choi et al 48 (R)-mandelic acid (30) is a key intermediate for the production of semi-synthetic cephalosporins and penicillins. 49 It can also be used as a chiral resolving agent and chiral synthon for the synthesis of anti-tumor and anti-obesity agents.…”

Section: Enzymatic Esterificationmentioning

confidence: 99%

Chemoenzymatic and microbial dynamic kinetic resolutions

et al. 2008

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This review tracks a decade of dynamic kinetic resolution developments with a biocatalytic inclination using enzymatic/microbial means for the resolution part followed by the racemization reactions either by means of enzymatic or chemocatalyst. These fast developments are due to the ability of the biocatalysts to significantly reduce the number of synthetic steps which are common for conventional synthesis. Future developments in novel reactions and products of dynamic kinetic resolutions should consider factors that are needed to be extracted at the early synthetic stage to avoid inhibition at scale-up stage have been highlighted.

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Biocatalytic enantioconvergent separation of racemic mandelic acid

Cited by 32 publications

References 10 publications

Rationally re-designed mutation of NAD-independent l-lactate dehydrogenase: high optical resolution of racemic mandelic acid by the engineered Escherichia coli

Rationally re-designed mutation of NAD-independent l-lactate dehydrogenase: high optical resolution of racemic mandelic acid by the engineered Escherichia coli

Enzymatic membrane reactors: the determining factors in two separate phase operations

Chemoenzymatic and microbial dynamic kinetic resolutions

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