Development of beta-Amino Acid Dehydrogenase for the Synthesis of beta-Amino Acids via Reductive Amination of beta-Keto Acids

Zhang Dalong; Chen Xi; Zhang Rui; Yao Peiyuan; Wu Qiaqing; Zhu Dunming

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Development of beta-Amino Acid Dehydrogenase for the Synthesis of beta-Amino Acids via Reductive Amination of beta-Keto Acids

机译：开发通过β-酮酸的还原胺合成β-氨基酸的β-氨基酸脱氢酶

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An L-erythro-3,5-diaminohexanoate dehydrogenase from Candidatus Cloacamonas acidaminovorans (3,5-DAHDHcca) was engineered to beta-amino acid dehydrogenase (beta-AADH) by screening a domain scanning mutagenesis library. The best beta-AADH mutant displayed about 200-fold activity toward (R)-beta-homomethionine compared with the wild-type enzyme. (R)-beta-Homomethionine, (R)-beta-phenylalanine, and (S)-beta-aminobutyric acid were obtained via beta-AADH-catalyzed reductive amination of the corresponding beta-keto acids, which were generated from beta-keto-nitriles or beta-keto-esters with nitrilase or lipase. This is the first example of the direct reductive amination of beta-keto acids catalyzed by beta-AADH to give beta-amino acids, opening a new venue for the synthesis of chiral beta-amino acids.

机译：通过筛选结构域扫描诱变文库，将来自Closidamonata cloacamonas acidaminovorans（3,5-DAHDHcca）的L-赤型3,5-二氨基己酸脱氢酶改造为β-氨基酸脱氢酶（β-AADH）。与野生型酶相比，最佳的β-AADH突变体对（R）-β-高甲硫氨酸的活性约为200倍。（R）-β-高甲硫氨酸，（R）-β-苯丙氨酸和（S）-β-氨基丁酸是通过β-AADH催化的相应β-酮酸的还原胺化反应而获得的，这些胺由β-酮生成-腈或β-酮酸酯与腈水解酶或脂肪酶。这是由β-AADH催化的β-酮酸直接还原胺化得到β-氨基酸的第一个例子，为合成手性β-氨基酸开辟了新的场所。

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《ACS catalysis》 |2015年第4期|共5页
作者
Zhang Dalong; Chen Xi; Zhang Rui; Yao Peiyuan; Wu Qiaqing; Zhu Dunming;
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正文语种 eng
中图分类物理化学（理论化学）、化学物理学;
关键词
asymmetric catalysis; beta-amino acid dehydrogenase; beta-amino acid; biocatalysis; reductive amination; enzyme engineering;

机译：不对称催化;β-氨基酸脱氢酶;β-氨基酸;生物催化;还原胺化;酶工程;

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专利

1. Development of beta-Amino Acid Dehydrogenase for the Synthesis of beta-Amino Acids via Reductive Amination of beta-Keto Acids [J] . Zhang Dalong, Chen Xi, Zhang Rui, ACS catalysis . 2015,第4期

机译：开发通过β-酮酸的还原胺合成β-氨基酸的β-氨基酸脱氢酶
2. Enantioselective synthesis of beta-amino acids. Part 9: Preparation of enantiopure alpha,alpha-disubstituted beta-amino acids from 1-benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one [J] . Juaristi E., Ramirez-Quiros Y., Balderas M. Tetrahedron, Asymmetry: The International Journal for Repid Publication on all Aspects of Asymmetry in Orgainc, Inorganic, Organometallic, Physical and Bio-Organic Chemistry . 1998,第21期

机译：β-氨基酸的对映选择性合成。第9部分：由1-苯甲酰基-2（S）-叔丁基-3-甲基全氢嘧啶-4-酮制备对映体纯的α，α-二取代的β-氨基酸
3. Enzymatic Synthesis of Enantiopure alpha- and beta-Amino Acids by Phenylalanine Aminomutase-Catalysed Amination of Cinnamic Acid Derivatives [J] . Wu B, Szymanski W, Wietzes P, Chembiochem: A European journal of chemical biology . 2009,第2期

机译：苯丙氨酸氨基变位酶催化的肉桂酸衍生物胺化酶合成对映体纯的α-和β-氨基酸
4. ExD fragmentation of peptides containing beta-amino acids including isoaspartate and cyclic beta-amino acids [C] . Nadezda P. Sargaeva, Cheng Lin, Konstantin Aizikov, American Society for Mass Spectrometry Conference on Mass Spectrometry and Allied Topics . 2010

机译：含有β-氨基酸的肽的蛋白质的碎片化，包括异菠寨酸盐和环状β-氨基酸
5. Constrained beta-prolines. (I) Methanopyrrolidine beta-amino acids: Synthesis and chracterization of novel C6-substituted analogues and peptide oligomers. (II) Synthesis of 2,2-disubstituted pyrrolidine-3-carboxylic acids. [D] . Hu, Zilun. 2015

机译：受约束的β-脯氨酸。（I）甲基吡咯烷β-氨基酸：新型C6取代的类似物和肽低聚物的合成和表征。（II）2，2-二取代的吡咯烷-3-羧酸的合成。
6. Transaminases for the synthesis of enantiopure beta-amino acids [O] . Jens Rudat, Birgit R Brucher, Christoph Syldatk 2012

机译：转氨酶用于合成对映纯的β-氨基酸
7. Homologation of alpha-amino acids to beta-amino acids using Fmoc-amino acid pentafluorophenyl esters [O] . Sureshbabu, V.V., Gopi, H.N., Ananda, K. 1999

机译：使用Fmoc-氨基酸五氟苯酯将α-氨基酸同化为β-氨基酸
8. Biostable beta-Amino Acid PK/PBAN Analogs: Agonist and Antagonist Properties [R] . Nachman, R J, Ben Aziz, O, Davidovitch, M, 2009

机译：生物稳定的β-氨基酸pK / pBaN类似物：激动剂和拮抗剂性质

Development of beta-Amino Acid Dehydrogenase for the Synthesis of beta-Amino Acids via Reductive Amination of beta-Keto Acids

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