Determining a novel NAD+-dependent amine dehydrogenase with a broad substrate range from Streptomyces virginiae IFO 12827: purification and characterization

Itoh, Nobuhide; Yachi, Chisato; Kudome, Tomomi

doi:10.1016/s1381-1177(00)00111-9

Cited by 57 publications

(47 citation statements)

References 21 publications

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“…[40] Remarka- www.chemcatchem.org bly, this enzyme converts a very broad range of substrates, such as amino alcohols, aliphatic amines, benzylic amines (only a-methylbenzylamine, a-MBA, was reported), and a-amino acids at comparable activity. Of known amine dehydrogenases, only one enzyme, which was recently purified from Streptomyces virginiae, accepts NADH as a cofactor.…”

Section: Asymmetric Synthesis With Amine Dehydrogenasesmentioning

confidence: 99%

Biocatalytic Routes to Optically Active Amines

2009

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Scheme 1. Asymmetric hydrogenation and addition are the two main synthetic strategies in the chemical preparation of a-chiral primary amines. If chiral auxiliaries are used to generate enantioselectivity, R 3 represents a chiral substituent. Deprotection is an important step in obtaining the desired amine, so the choice of a readily cleavable group, such as diphenylphosphinyl or tert-butylsulfinyl, is recommended. [23] Scheme 2. Summary of possible enzymatic routes to optically active a-chiral amines.Scheme 6. Asymmetric synthesis of (S)-2-amino-1-methoxypropane.

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Section: Asymmetric Synthesis With Amine Dehydrogenasesmentioning

confidence: 99%

Biocatalytic Routes to Optically Active Amines

2009

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“…Until now, only one NAD + -dependent AmDH found in nature has been reported, in Streptomyces virginiae, but it showed poor enantioselectivity and its DNA information is not available [15]. Recently, AmDHs have been created through protein engineering using the existing L-amino acid dehydrogenase.…”

Section: Introductionmentioning

confidence: 99%

The Kinetic Resolution of Racemic Amines Using a Whole-Cell Biocatalyst Co-Expressing Amine Dehydrogenase and NADH Oxidase

et al. 2017

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Amine dehydrogenase (AmDH) possesses tremendous potential for the synthesis of chiral amines because AmDH catalyzes the asymmetric reductive amination of ketone with high enatioselectivity. Although a reductive application of AmDH is favored in practice, the oxidative route is interesting as well for the preparation of chiral amines. Here, the kinetic resolution of racemic amines using AmDH was first extensively studied, and the AmDH reaction was combined with an NADH oxidase (Nox) to regenerate NAD + and to drive the reaction forward. When the kinetic resolution was carried out with 10 mM rac-2-aminoheptane and 5 mM rac-α-methylbenzylamine (α-MBA) using purified enzymes, the enantiomeric excess (ee) values were less than 26% due to the product inhibition of AmDH by ketone and the inhibition of Nox by the substrate amine. The use of a whole-cell biocatalyst co-expressing AmDH and Nox apparently reduces the substrate and product inhibition, and/or it increases the stability of the enzymes. Fifty millimoles (50 mM) rac-2-aminoheptane and 20 mM rac-α-MBA were successfully resolved into the (S)-form with >99% ee using whole cells. The present study demonstrates the potential of a whole-cell biocatalyst co-expressing AmDH and Nox for the kinetic resolution of racemic amines.

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“…[1] In 2000, 35 % of APIs were chiral compounds, and this number was expected to increase to 70 % by 2010. [4] While chiral amines can be produced both chemically and enzymatically, the large-scale production of chiral amines is still challenging and heavily reliant on traditional methods of chemical synthesis. A recent assessment by the ACS Green Chemistry Institute, Pharmaceutical Roundtable noted that the asymmetric synthesis of amines from prochiral ketones and free ammonia was one of the top aspirational reactions challenging the pharmaceutical industry.…”

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confidence: 99%