Deracemisation and stereoinversion of α-amino acids using D-amino acid oxidase and hydride reducing agents

Beard, Timothy M.; Turner, Nicholas J.

doi:10.1039/b107580m

Cited by 94 publications

(48 citation statements)

References 10 publications

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“…[92,93] Thus, using l-amino acid oxidase from Proteus myxofaciens and various amine-borane complexes, [94] or d-amino acid oxidase from porcine kidney and sodium cyanoborohydride, [95] the preparation of several natural and non-natural enantiopure d-and l-amino acids was achieved, respectively. In a more recent report, several b-and gsubstituted a-amino acids were deracemized using damino acid oxidase from Trigonopsis variabilis and sodium cyanoborohydride or sodium borohydride.…”

Section: Combining An Oxidase With a Chemical Reducing Agentmentioning

confidence: 99%

From a Racemate to a Single Enantiomer: Deracemization by Stereoinversion

et al. 2006

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Abstract:The stereoinversion of one enantiomer into its mirror-image counterpart within a racemate furnishes a single stereoisomeric product in 100 % theoretical yield. This extremely efficient type of deracemization, whereby substrate and product possess an identical chemical structure, can be achieved by using bio-or chemo-catalysts or combinations thereof and is applicable to secondary alcohols, amines and a-substituted carboxylic acids. Special emphasis is devoted to the theoretical background of the onepot, single-step deracemization of sec-alcohols.

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Section: Combining An Oxidase With a Chemical Reducing Agentmentioning

confidence: 99%

From a Racemate to a Single Enantiomer: Deracemization by Stereoinversion

et al. 2006

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“…DAAO is widely used in biosensors for determination of D amino acids in biological samples, including nervous tissue, 34 for the separation of racemic mixtures of amino acids, 35 and in the synthesis of α keto acids. 36 Selection of the source. Despite the fact that the en zyme DAAO was discovered in the 1930s, it is still poorly studied, and the available experimental data are often contradictory.…”

Section: Development Of the Methods For Isolation Of The Enzyme And Prmentioning

confidence: 99%

Creation of biocatalysts with prescribed properties

2008

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Oxidoreductases are widely used in different branches of industry (particularly, in pharma ceutical) and analytical biotechnology. To optimize the use and to reduce production cost of a target product, the properties of a biocatalyst should be modified to meet requirements of a specific process or method of analysis. Problem of creation of biocatalysts with prescribed properties includes complex set of R&D such as an engineering of enzyme properties, con struction of recombinant strains overproducing the target protein, development of a large scale downstream process and preparation of a working form of a biocatalysts. In the present work, the basic features and practical examples of such an over all approach are considered for formate dehydrogenase and D amino acid oxidase.

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“…[168]. The key success factor is to have the reducing agent compatible with the enzyme [169,170]. Rather than use the antipode of the desired product, the racemic mixture can be used as the starting material.…”

Section: Amino Acid Oxidasesmentioning

confidence: 99%