Enzymic conversion of .alpha.-keto aldehydes to optically active .alpha.-hydroxy acids using glyoxalase I and II

Patterson, Mark; Szajewski, Richard P.; Whitesides, George M.

doi:10.1021/jo00336a011

Cited by 40 publications

(13 citation statements)

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“…Currently, R-MA is produced by optical resolution of the racemate with chiral amines, and the maximum theoretical yield of the desired product is only 50% [18]. For the production of the enantiomerically pure R-MA with higher yield, various biological routes have been studied: (i) microbiological hydrolysis of mandelic acid derivatives [19]; (ii) asymmetric reduction of benzoylformic acid with microorganisms [17]; (iii) microbial oxidation of 1-phenyl-1,2-ethanediol [11]; (iv) enzymatic asymmetric synthesis from a-keto aldehyde [12]; (v) microbial oxidation of racemic mandelic acid [10]; (vi) biotransformation of (R,S)-mandelonitrile with nitrilase [20]. Industrial application of the last of these methods is attractive because of its excellent enantioselectivity, cheap starting material which can be synthesized from benzaldehyde by a single step, and above all a possibility of carrying out a dynamic kinetic resolution of substrate which provides theoretically 100% yield of the product (Fig.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(−)-mandelic acid by a newly isolated mutant strain

Xue

Liu

et al. 2010

J Ind Microbiol Biotechnol

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(R)-(-)-Mandelic acid (R-MA) is an important intermediate with broad uses. Recently, R-MA production using nitrilase has been gaining more and more attention due to its higher productivity and enantioselectivity. In this work, a new bacterium WT10, which exhibited favorable nitrilase activity and excellent enantioselectivity for production of R-MA by enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile, was isolated and identified as a strain of Alcaligenes faecalis. In order to improve its nitrilase activity for industrial application, the wild-type strain WT10 was further subjected to mutagenesis using a combined LiCl-ultraviolet irradiation and low energy N(+) ion beams implantation technique. A valuable mutant strain A. faecalis ZJUTB10 was obtained. The nitrilase specific activity of the mutant strain was greatly improved up to 350.8 U g(-1), in comparison with wild-type strain WT10 of 53.09 U g(-1). The reaction conditions for R-MA production by mutant strain A. faecalis ZJUTB10 were also optimized. Nitrilase activity in mutant strain showed a broad pH optimum at pH 7.7-8.5. The optimal temperature was 35°C. The highest production rate reached 9.3 mmol h(-1) g(-1). The results showed that mutant strain A. faecalis ZJUTB10 was a new candidate for efficient R-MA production from (R,S)-mandelonitrile and could potentially be used in industrial production.

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Section: Introductionmentioning

confidence: 99%

Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(−)-mandelic acid by a newly isolated mutant strain

Xue

Liu

et al. 2010

J Ind Microbiol Biotechnol

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“…Further, they are also used in the prevention and treatment of honeybee diseases, for human and animal toxoplasmosis and in the synthesis of agrochemicals. R‐(−)‐mandelic acid has been prepared by the microbiological hydrolysis of mandelic acid derivatives,25, 26 asymmetric reduction of benzoylformic acid with microorganisms,27 microbial oxidation of 1‐phenyl‐1,2‐ethanediol,28 microbial oxidation of racemic mandelic acid29 and enzymatic asymmetric synthesis from n ‐keto aldehyde 30. Enzymatic asymmetric synthesis has been explored.…”

Section: Introductionmentioning

confidence: 99%

Novel Hybrid Esterase‐Haloacid Dehalogenase Enzyme

et al. 2010

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“…R-(−)-mandelic acid has been prepared by the microbiological hydrolysis of mandelic acid derivatives, 25,26 asymmetric reduction of benzoylformic acid with microorganisms, 27 microbial oxidation of 1-phenyl-1,2-ethanediol, 28 microbial oxidation of racemic mandelic acid 29 and enzymatic asymmetric synthesis from n-keto aldehyde. 30 Enzymatic asymmetric synthesis has been explored. Benzaldehyde can be converted into enantiomerically pure (S)-mandelic acid by sequential HCN addition and hydrolysis using a bienzymatic oxynitrilase-nitrilase cascade.…”

Section: Introductionmentioning

confidence: 99%

Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of RS‐( ± )‐methyl mandelate

Yadav

Sajgure

Dhoot

2008

J of Chemical Tech & Biotech

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BACKGROUND: Mandelic acid enantiomers are important chiral analogs used for the resolution of racemic alcohols and amines. R-(−)-mandelic acid is a precursor for the production of semi-synthetic penicillins and cephalosporins and also for the synthesis of various pharmaceuticals. Production of optically pure mandelic acid enantiomers is commercially significant. This work deals with the resolution of RS-(±)-methyl mandelate to produce optically pure R-(−)-mandelic acid in non-aqueous media via lipase-catalyzed hydrolysis under microwave irradiation.

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Enzymic conversion of .alpha.-keto aldehydes to optically active .alpha.-hydroxy acids using glyoxalase I and II

Cited by 40 publications

References 0 publications

Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(−)-mandelic acid by a newly isolated mutant strain

Enantioselective biocatalytic hydrolysis of (R,S)-mandelonitrile for production of (R)-(−)-mandelic acid by a newly isolated mutant strain

Novel Hybrid Esterase‐Haloacid Dehalogenase Enzyme

Insight into microwave irradiation and enzyme catalysis in enantioselective resolution of RS‐( ± )‐methyl mandelate

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