L-β-2-chlorophenylserine

• 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: L-β-2-chlorophenylserine
• 英文别名: o-chlorophenylserine；(2S,3R)-2-amino-3-(2-chlorophenyl)-3-hydroxypropanoic acid；(2S,3R)-2-amino-3-hydroxy-3-(o-chlorophenyl)propanoic acid
• 化学式: C₉H₁₀ClNO₃
• 分子量: 215.636
• InChiKey: IHNIQIZZORTGDJ-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  14
• 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：
  83.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (1S,2R,5S,8R,1'R)-5-(1'-hydroxy-o-chlorobenzyl)-8,11,11-trimethyl-3-oxa-6-azatricyclo[6.2.1.0(2,7)]undec-6-en-4-one 在 盐酸 、 水 作用下， 反应 3.0h， 以76%的产率得到L-β-2-chlorophenylserine
  参考文献：
  名称：

  β-羟基-α-氨基酸的非对映体和对映体选择性合成：在乳酸菌素关键中间体合成中的应用

  摘要：

  描述了用于制备β-羟基-α-氨基酸的高效和立体选择方法的发展。在−78°C的条件下，在THF中存在6当量氯化锂的情况下，将三环亚氨基内酯1a和1b的烯酸酯亲核加成到醛中，得到高收率（63-86％）和高非对映选择性（高达> 25的醛醇加合物）： 1博士）。随后，在酸性条件下醛醇加合物的水解导致相应的β-羟基-α-氨基酸以良好的产率（高达83％）和优异的对映体过量（99％ee）具有良好的手性助剂6和7的回收率。7。该方法学适用于乳酸菌素关键中间体及其几种异构体的简便合成。

  DOI：

  10.1021/jo8023973

文献信息

• Improving and Inverting C_β-Stereoselectivity of Threonine Aldolase via Substrate-Binding-Guided Mutagenesis and a Stepwise Visual Screening
  作者：Qijia Chen、Xi Chen、Jinhui Feng、Qiaqing Wu、Dunming Zhu、Yanhe Ma

  DOI：10.1021/acscatal.9b00859

  日期：2019.5.3

  Threonine aldolase (TA)-catalyzed aldol condensation is a powerful tool for C–C bond formation under mild conditions, but the low Cβ-stereoselectivity has hampered its wide application. A stepwise visual screening method was developed to measure the activity and stereoselectivity of threonine aldolase-catalyzed aldol condensation by employing a stereoselective phenylserine dehydratase, enabling direct

  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。
• 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
• Production and properties of threonine aldolase immobilisates
  作者：Sandra Kurjatschij、Michael Katzberg、Martin Bertau

  DOI：10.1016/j.molcatb.2014.01.021

  日期：2014.5

  Dichiral beta-hydroxy-alpha-amino acids are a highly valuable class of compounds from which pharmaceutically active intermediates for the synthesis of e.g. beta-sympathomimetic drugs can be obtained. In lieu of laborious multi-step "classical" organic synthesis, biocatalysis using threonine aldolases (TAs) opens up a way to synthesise beta-hydroxy-alpha-amino acids in one step. Although enzyme kinetics, stereospecificity as well as substrate specificity were and are matters of investigation, there is a lack of investigations addressing enzyme stability, which is crucial if the reaction is thought to be transferred to an economical scale.Hence methods to immobilise the L-low specificity threonine aldolase of Escherichia coli (L-TA) were studied. After extensive screening the entrapment of the enzyme into a porous network of orthosilicate appeared to be the most promising method. (C) 2014 Elsevier B.V. All rights reserved.
• 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.
• A study towards efficient l-threonine aldolase-catalyzed enantio- and diastereoselective aldol reactions of glycine with substituted benzaldehydes: biocatalyst production and process development
  作者：Katrin Baer、Nina Dückers、Thorsten Rosenbaum、Christian Leggewie、Sabine Simon、Marina Kraußer、Steffen Oßwald、Werner Hummel、Harald Gröger

  DOI：10.1016/j.tetasy.2011.04.016

  日期：2011.5

  The development of aldol reactions of glycine with substituted benzaldehydes in the presence of recombinant L-threonine aldolases from Escherichia coli or Saccharomyces cerevisiae, which were obtained with excellent overexpression data, has been carried out. When using glycine and ortho-chlorobenzaldehyde, a high conversion of >95%, an enantioselectivity of >99% ee, and a diastereoselectivity with d.r.(syn/anti) = 80:20 was obtained for the resulting beta-hydroxy alpha-amino acid in such a biotransformation. It should be noted that this enzymatic process can be conducted at an elevated substrate concentration of 250 mM. (C) 2011 Elsevier Ltd. All rights reserved.