(2S,3R)-2-amino-5-(benzyloxy)-3-hydroxyvaleric acid | 78314-64-4

• 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-5-(benzyloxy)-3-hydroxyvaleric acid
• 英文别名: (2S,2R)-2-amino-5-(benzyloxy)-3-hydroxypentanoic acid；rel-(3S)-3-Hydroxy-5-(phenylmethoxy)-D-norvaline；(2S,3R)-2-amino-3-hydroxy-5-phenylmethoxypentanoic acid
• CAS: 78314-64-4
• 化学式: C₁₂H₁₇NO₄
• 分子量: 239.271
• InChiKey: BBOKOCJCFAOTKE-MNOVXSKESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  92.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-苄氧基-1-丙醇 在 sodium hypochlorite 、 2,2,6,6-四甲基哌啶氧化物 、 1,4-dithio-D,L-threitol 、 glycine hydroxymethyltransferase 、 磷酸吡哆醛 、 碳酸氢钠 、 sodium bromide 、 sodium hydroxide 作用下， 以 水 、 乙酸乙酯 、 甲苯 为溶剂， 反应 24.0h， 生成 (2S,3S)-2-amino-5-(benzyloxy)-3-hydroxypentanoic acid 、 (2S,3R)-2-amino-5-(benzyloxy)-3-hydroxyvaleric acid
  参考文献：
  名称：

  化学酶促合成苏-和赤-β-羟基-1-谷氨酸衍生物的研究

  摘要：

  丙二醛半醛的衍生物通过酶I-苏氨酸醛缩酶催化的生物转化从大肠杆菌转化为两种β-羟基谷氨酸前体的6：4差向异构体混合物。该酶对形成（S）-C-2处的配置，而C-3处的配置不受控制。利用脂肪酶PS催化的有机溶剂中的非对映选择性酰化作用分离了两种差向异构体。在Kazslauskas提出的脂肪酶PS的立体偏好模型的基础上，并通过比较两个同系物的H-2和H-3质子的化学位移，初步确定了产物的相对和绝对构型。证明了通过常规化学反应将获得的产物转化为β-羟基谷氨酸衍生物的可能性。

  DOI：

  10.1016/j.molcatb.2011.11.004

文献信息

• Enzymatic Synthesis of β-Hydroxy-α-amino Acids Based on Recombinant <scp>d</scp>- and <scp>l</scp>-Threonine Aldolases
  作者：Teiji Kimura、Vassil P. Vassilev、Gwo-Jenn Shen、Chi-Huey Wong

  DOI：10.1021/ja9720422

  日期：1997.12.1

  To exploit the enzymatic method for the synthesis of β-hydroxy-α-amino acids, the genes coding for the Escherichia coli l-threonine aldolase (LTA; EC 2.1.2.1) and Xanthomonus oryzae d-threonine aldolase (DTA) were cloned and overexpressed in E. coli through primer-directed polymerase chain reactions. The purified recombinant enzymes were studied with respect to kinetics, specificity, stability, additive

  为了利用酶促方法合成 β-羟基-α-氨基酸，克隆了编码大肠杆菌 l-苏氨酸醛缩酶 (LTA；EC 2.1.2.1) 和米黄杆菌 d-苏氨酸醛缩酶 (DTA) 的基因，并通过引物指导的聚合酶链反应在大肠杆菌中过表达。研究了纯化的重组酶的动力学、特异性、稳定性、添加剂要求、温度分布和 pH 依赖性。DTA 需要镁离子作为辅助因子，而 LTA 不需要金属离子。这些酶在浓度高达 40% 的 DMSO 存在下工作良好，并且观察到 DMSO 诱导的 LTA 催化反应的速率加速。这两种酶都使用磷酸吡哆醛辅酶来激活甘氨酸以与多种醛反应。LTA 得到赤-β-羟基-α-l-氨基酸与脂肪醛和苏式异构体与芳香醛作为动力学控制的产物。另一方面，DTA 形成苏-β-羟基-α-d-氨基酸作为动力学c...
• Kinetic and thermodynamic control of L-Threonine aldolase catalyzed reaction and its application to the synthesis of mycestericin D
  作者：Kayoko Shibata、Kazushi Shingu、Vassil P. Vassiley、Kiyoharu Nishide、Tetsuro Fujita、Manabu Node、Tetsuya Kajimoto、Chi-Huey Wong

  DOI：10.1016/0040-4039(96)00430-3

  日期：1996.4

  L-Threonine aldolase catalyzes the aldol condensation of γ-benzyloxybutanal and glycine with high erythrolthreo selectivity under a kinetically controlled condition. The erythro product was used in the synthesis of mycestericin D, a potent immunosupressant.

  L-苏氨酸醛缩酶在动力学控制的条件下以高的赤藓糖基选择性催化γ-苄氧基丁醛和甘氨酸的醛醇缩合。该赤产物在mycestericin d，一种有效的免疫抑制剂的合成中使用。
• 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.