(2S,3R)-2-amino-1,3,4-butanetriol | 62397-88-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (2S,3R)-2-amino-1,3,4-butanetriol
• 英文别名: 2-amino-2-deoxy-threitol；Threosaminitol；(2R,3S)-3-aminobutane-1,2,4-triol
• CAS: 62397-88-0；83168-64-3；87069-32-7；111453-48-6；111554-89-3
• 化学式: C₄H₁₁NO₃
• 分子量: 121.136
• InChiKey: PMLGQXIKBPFHJZ-IMJSIDKUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  86.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  L(+)-赤藓酮糖(水合) 在 transaminase 、 磷酸吡哆醛 、 异丙胺 作用下， 生成 (2S,3R)-2-amino-1,3,4-butanetriol
  参考文献：
  名称：

  一种用于快速评估多步酶促合成的工具箱方法，包括“混合和匹配”E。带有微型实验的大肠杆菌表达系统

  摘要：

  摘要 这项工作描述了一个实验“工具箱”，用于快速评估和优化多步酶合成，包括“混合匹配”基于大肠杆菌的表达系统和自动化微孔规模实验。该方法通过使用转酮酶 (TK) 和转氨酶 (TAm) 分别催化不对称碳-碳键形成和选择性手性胺基加成来合成光学纯氨基醇的从头设计途径进行说明。大肠杆菌表达系统基于两个相容的质粒，能够评估来自先前设计和克隆的 TK 和 TAm 文库中的酶对，以评估不同初始底物的顺序转化。这与微孔实验相辅相成，可以有效研究不同的生物催化剂形式、不同胺供体的使用和底物进料策略。使用此实验性“工具箱”，一锅合成非对映异构体 (2S,3S)-2-aminopentane-1,3-diol (APD) 和 (2S,3R)-2-amino-1,3,4-butanetriol (ABT) 的设计和执行，在 25 小时内，APD 的最终产品产率为 90% mol/mol，ABT 的最终产品产率为

  DOI：

  10.3109/10242422.2011.609589

文献信息

• Characterization of a novel amine transaminase from Halomonas elongata
  作者：Lorenzo Cerioli、Matteo Planchestainer、Jennifer Cassidy、Davide Tessaro、Francesca Paradisi

  DOI：10.1016/j.molcatb.2015.07.009

  日期：2015.10

  Chiral amines are indispensable building blocks in the production of biologically active compounds. They are fundamental for the pharmaceutical industry, both as active molecules themselves and as chiral auxiliaries in asymmetric synthesis; however, the available synthetic strategies often present disadvantages. omega-Transaminases (omega-TAs) appear as an attractive alternative by driving the stereoselective amination of prochiral ketones. HEWF is a novel amine transaminase from the moderate halophilic bacterium, Halomonas elongate DSM 2581, which is highly (S)-selective, being able to fully convert (S)-1-phenylethylamine to acetophenone and showing no activity with the corresponding (R)-1-phenylethylamine. HEWF has a broad substrate scope, active with a range of amino donors and acceptors, and naturally accepts isopropylamine (IPA) as amino donor in asymmetric synthesis providing a 41% conversion of pyruvate in 24 h at 37 degrees C starting with 1:1 molar ratio between the reagents. HEWF also accepts ortho-xylylenediamine as amino donor in for amine synthesis, in particular, with benzaldehyde yielding high conversions between 90 and 95%. The enzyme is also tolerant to the presence of cosolvents up to 20% making it a promising candidate for industrial applications. (C) 2015 Elsevier B.V. All rights reserved.
• Preparation of enantioenriched tetraols and triolamines from a common epoxide
  作者：Makan Kaviani-Joupari、Michael P. Schramm

  DOI：10.1016/j.tetlet.2013.07.001

  日期：2013.9

  We identify a silylcyclopentene oxide that is amenable to several distinct asymmetric catalytic transformations providing access to enantio-enriched tetraol and triol-amines. The sequence employed allows for selective protection of one amine or alcohol from the four heteroatoms that are introduced into the carbon scaffold. (C) 2013 Elsevier Ltd. All rights reserved.
• 2,3-Diacetamido-2,3-dideoxy-d-mannuronic acid and its 2-imidazoline derivative: new acidic amino sugars from Pseudomonas aeruginosa O: 3a,d lipopolysaccharide
  作者：Yuriy A. Knirel、Evgeniy V. Vinogradov、Alexander S. Shashkov、Boris A. Dmitriev、Nikolay K. Kochetkov

  DOI：10.1016/s0008-6215(00)82229-6

  日期：1982.6