(2S,3R)-2-amino-3-hydroxy-3-(3-nitrophenyl)propanoic acid

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3R)-2-amino-3-hydroxy-3-(3-nitrophenyl)propanoic acid
• 英文别名: L-β-3-nitrophenylserine；(2S,3R)-2-azaniumyl-3-hydroxy-3-(3-nitrophenyl)propanoate
• 化学式: C₉H₁₀N₂O₅
• 分子量: 226.189
• InChiKey: MBHARJQAJLMPIU-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间硝基苯甲醛 、 聚甘氨酸 在 磷酸吡哆醛 、 Pseudomonas sp. L-threonine aldolase D₉₃H/E₁₄₇D mutant 作用下， 以 二甲基亚砜 为溶剂， 反应 12.0h， 以38%的产率得到
  参考文献：
  名称：

  改善和反相Ç β经由底物结合制导诱变和一个逐步的视觉筛选醛缩酶苏氨酸的-Stereoselectivity

  摘要：

  苏氨酸醛缩酶（TA） -催化的醛醇缩合为温和的条件下C-C键形成的有力工具，但低C β -stereoselectivity已经阻碍其广泛应用。甲逐步视觉筛选方法被开发醛缩酶-催化的醛醇缩合通过采用立体选择性苯基丝氨酸脱水酶，使突变体的直接选择与较高的C测量苏氨酸的活性和立体选择性β -stereoselectivity。假单胞菌的1- PsTA突变体sp。通过同时突变与底物的氨基和羟基相互作用的氨基酸残基，并用此方法筛选所得的突变体文库，可以获得对芳香族醛具有改善的或反向的立体选择性的化合物。所述突变和酶-底物对接研究提供了一些见解到C的调节β -stereoselectivity通过酶-底物相互作用。这项研究提供的工具和有用的指导助教的进一步工程，以解决与c β -stereoselectivity问题。

  DOI：

  10.1021/acscatal.9b00859

文献信息

• Application of Threonine Aldolases for the Asymmetric Synthesis of α-Quaternary α-Amino Acids
  作者：Julia Blesl、Melanie Trobe、Felix Anderl、Rolf Breinbauer、Gernot A. Strohmeier、Kateryna Fesko

  DOI：10.1002/cctc.201800611

  日期：2018.8.21

  acids with perfect stereoselectivity for the α‐quaternary center through the action of l‐ and d‐specific threonine aldolases. A wide variety of aliphatic and aromatic aldehydes were accepted by the enzymes and conversions up to >80 % were obtained. In the case of d‐selective threonine aldolase from Pseudomonas sp., generally higher diastereoselectivities were observed. The applicability of the protocol

  我们报道了通过l-和d-特异性苏氨酸醛缩酶的作用，合成了多种 β-羟基-α,α-二烷基-α-氨基酸，对 α-四元中心具有完美的立体选择性。酶可以接受多种脂肪族和芳香族醛，并且转化率高达 >80%。对于来自假单胞菌属的d-选择性苏氨酸醛缩酶，通常观察到较高的非对映选择性。通过以制备规模进行酶促反应证明了该方案的适用性。使用假单胞菌属的d-苏氨酸醛缩酶，用非对映异构体一步生成制备量的 (2 R ,3 S )-2-氨基-3-(2-氟苯基)-3-羟基-2-甲基丙酸比率 >100 有利于顺式产品。 Birch型还原能够从( 2S )-2-氨基-3-羟基-2-甲基-3-苯基丙酸中还原除去β-羟基，通过两个反应生成对映体纯l -α-甲基-苯丙氨酸。 ‐一步化学酶转化。
• Characteristics of <scp>l</scp>-threonine transaldolase for asymmetric synthesis of β-hydroxy-α-amino acids
  作者：Lian Xu、Li-Chao Wang、Xin-Qi Xu、Juan Lin

  DOI：10.1039/c9cy01608b

  日期：——

  L-threo-β-hydroxy-α-amino acid so far reported by enzymatic synthesis. Finally, synthesis of L-threo-p-methylsulfonylphenylserine at a 100 mL scale by whole-cell biocatalysis was conducted. This is the first systematic report of L-threonine transaldolase as a robust biocatalyst for preparation of β-hydroxy-α-amino acids, which can provide new insights for β-hydroxy-α-amino acids synthesis.

  L-苏氨酸转醛酶（LTTA）是一种推定的丝氨酸羟甲基转移酶（SHMT），可以催化L-苏氨酸和醛的反式-醛反应，产生具有出色立体选择性的L-苏式-β-羟基-α-氨基酸。在本研究中，来自假单胞菌属（Pseudomonas sp。）的L-苏氨酸转醛酶。（PsLTTA）被开采并在大肠杆菌BL21（DE3）中表达。底物光谱测定表明，PsLTTA仅消耗L-苏氨酸作为供体底物，并且可以接受多种芳族醛作为受体底物。在这些底物中，PsLTTA可以催化p-甲基磺酰基苯甲醛和L-苏氨酸生产具有高转化率（74.4％）和高de值（79.9％）的L-苏-对-甲基磺酰基苯基丝氨酸。发现PsLTTA的转化率和立体选择性受整个细胞浓度，助溶剂和反应温度的显着影响。通过条件优化，获得了L-苏-对-甲基磺酰基苯基丝氨酸，其转化率为67.1％，de值接近完美（94.5％），这是迄今为止L-苏-β-羟基-α-氨基酸的最高立体选择性
• Threonine aldolases—an emerging tool for organic synthesis
  作者：Johannes Steinreiber、Kateryna Fesko、Christoph Reisinger、Martin Schürmann、Friso van Assema、Michael Wolberg、Daniel Mink、Herfried Griengl

  DOI：10.1016/j.tet.2006.11.035

  日期：2007.1

  In a systematic study, 21 ring-substituted benzaldehydes were reacted with glycine under catalysis with a L-threonine aldolase (LTA) from Pseudomonas putida and a D-threonine aldolase (DTA) from Alcaligenes xylosoxidans to form the corresponding beta-hydroxy-alpha-amino acids 1-18. DTA proved to be highly selective with ee's > 99% (D) and de's up to 99% (syn). Two thiamphenicol precursors were synthesized utilizing DTA on a preparative scale. LTA-catalyzed reactions led to ee's > 99% (L) but low to moderate de's (20-50%, syn). (c) 2006 Elsevier Ltd. All rights reserved.
• ENGINEERED ALDOLASE POLYPEPTIDES AND USES THEREOF
  申请人：Enzymaster (Ningbo) Bio-Engineering Co., Ltd

  公开号：US20200123525A1

  公开（公告）日：2020-04-23

  The present invention provides engineered polypeptides that are useful for the asymmetric synthesis of β-hydroxy-α-amino acids under industrial-relevant conditions. The present disclosure also provides polynucleotides encoding engineered polypeptides, host cells capable of expressing engineered polypeptides, and methods of producing β-hydroxy-α-amino acids using engineered polypeptides. Compared to other processes of preparation, the use of the engineered polypeptides of the present invention for the preparation of β-hydroxy-α-amino acids results in high purity of the desired stereoisomers, mild reaction conditions, low pollution and low energy consumption. So, it has good industrial application prospects.
• ENGINEERED POLYPEPTIDES AND THEIR APPLICATIONS IN THE SYNTHESIS OF BETA-HYDROXY-ALPHA-AMINO ACIDS
  申请人：Enzymaster (Ningbo) Bio-Engineering Co., Ltd.

  公开号：US20210284987A1

  公开（公告）日：2021-09-16

  The present invention provides engineered polypeptides that are useful for the asymmetric synthesis of β-hydroxy-α-amino acids under industrial-relevant conditions. The engineered polypeptides disclosed in this invention were developed through directed evolution based on the ability of catalytic synthesis of (2S, 3R)-2-amino-3-hydroxy-3-(4-nitrophenyl) propanoic acid. The present disclosure also provides polynucleotides encoding engineered polypeptides, host cells capable of expressing engineered polypeptides, and methods of producing β-hydroxy-α-amino acids using engineered polypeptides. Compared to other processes of preparation, the use of the engineered polypeptides of the present invention for the preparation of β-hydroxy-α-amino acids results in high purity of the desired stereoisomers, mild reaction conditions, low pollution and low energy consumption. So, it has good industrial application prospects.