1,3-dihydroxy-2-pentanone | 618911-92-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3-dihydroxy-2-pentanone
• 英文别名: (3R)-1,3-dihydroxypentan-2-one；(R)-1,3-dihydroxypentan-2-one
• CAS: 618911-92-5
• 化学式: C₅H₁₀O₃
• 分子量: 118.133
• InChiKey: PSVHBERWTCIGEC-SCSAIBSYSA-N

物化性质

• 沸点：
  223.3±15.0 °C(Predicted)
• 密度：
  1.140±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  hydroxypyruvate 、 丙醛 在 transketolase from Escherichia coli 、 焦磷酸硫胺素 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 3.0h， 以53%的产率得到
  参考文献：
  名称：

  对控制转酮醇酶立体选择性的因素的机械理解

  摘要：

  建立了硫胺二磷酸（ThDP）依赖性转酮酶（TK）的结构模型，以分析氨基酸交换对这种重要合成酶的立体选择性的影响。在这项研究中，研究了3-羟基丙酮酸作为供体和丙醛以及戊醛的碳结。基于文献数据和使用大肠杆菌的其他诱变研究TK是一种四态模型，旨在通过在形成CC键之前在活性位点中供体和受体底物的相对取向来解释TK的立体选择性。为了能够对不同物种的TK的相关氨基酸进行功能比较，开发了一种标准的编号方案。使用这个概念，H26，H261和F434被确定为介导立体选择性的关键残基，其中两个主要因素影响碳键化之前ThDP结合的供体和受体的排列：底物侧链的相对方向和受体羰基朝向供体羟基。该模型提供了第一个框架，用于了解传统知识与立体选择性之间的结构-功能关系。

  DOI：

  10.1002/cctc.201800299

文献信息

• Enhancing and Reversing the Stereoselectivity of<i>Escherichia coli</i>Transketolase<i>via</i>Single-Point Mutations
  作者：Mark E. B. Smith、Edward G. Hibbert、Alexander B. Jones、Paul A. Dalby、Helen C. Hailes

  DOI：10.1002/adsc.200800489

  日期：2008.11.3

  successfully applied to a 96-well format, and new active TK mutants were identified, which gave 1,3-dihydroxypentan-2-one in high stereoselectivities. Remarkably, active-site single-point mutants were identified that were able to both enhance and reverse the stereoselectivity of TK.

  已经开发了手性辅助方法和手性测定法，以建立使用野生型（WT）大肠杆菌转酮醇酶（TK）生成的赤藓糖和1,3-二羟基戊烷-2-酮的对映体纯度。在95％ee中形成L-赤藓糖，在58％ee中形成（3 S）-1,3-二羟基戊烷-2-一。由于后一种化合物是在中等ee中形成的筛选了TK文库以鉴定更高性能的突变体。比色筛选和手性测定已成功应用于96孔格式，并鉴定了新的活性TK突变体，从而产生了高立体选择性的1,3-二羟基戊烷-2-一。明显地，鉴定出能够增强和逆转TK的立体选择性的活性位点单点突变体。
• Modular microfluidic reactor and inline filtration system for the biocatalytic synthesis of chiral metabolites
  作者：Brian O'Sullivan、Homam Al-Bahrani、James Lawrence、Maria Campos、Armando Cázares、Frank Baganz、Roland Wohlgemuth、Helen C. Hailes、Nicolas Szita

  DOI：10.1016/j.molcatb.2011.12.010

  日期：2012.5

  Biocatalytic synthesis is now well established amongst catalytic methodologies as an extremely useful approach for the industrial synthesis of high-value compounds, due to its many advantages such as high reaction specificity and selectivity. However, engineering a biocatalytic process can be complex and time-consuming. This paper presents a modular microfluidic reactor and in-line filtration system for the rapid and small-scale evaluation of biocatalytic reactions. The system combines a substrate with a biocatalyst in free solution, incubates the two components until full conversion to product has been achieved, before extracting the product. The system has been applied to the transketolase-catalysed reaction of hydroxypyruvate (HPA) and glycolaldehyde (GA) to L-erythrulose, demonstrating complete conversion of substrate to product, complete retention of the enzyme and an overall yield of approximately 65%. The complete conversion of HPA and propanal to (3S)-1,3-dihydroxypentan-2-one with a mutant transketolase further demonstrated the applicability of the microfluidic system for organic synthesis. (C) 2012 Elsevier B.V. All rights reserved.
• A Multidisciplinary Approach Toward the Rapid and Preparative-Scale Biocatalytic Synthesis of Chiral Amino Alcohols: A Concise Transketolase-/ω-Transaminase-Mediated Synthesis of (2<i>S</i>,3<i>S</i>)-2-Aminopentane-1,3-diol
  作者：Mark E. B. Smith、Bing H. Chen、Edward G. Hibbert、Ursula Kaulmann、Kirsty Smithies、James L. Galman、Frank Baganz、Paul A. Dalby、Helen C. Hailes、Gary J. Lye、John M. Ward、John M. Woodley、Martina Micheletti

  DOI：10.1021/op900190y

  日期：2010.1.15

  Chiral amino alcohols represent an important class of value-added biochemicals and pharmaceutical intermediates. Chemical routes to such compounds are generally step intensive, requiring environmentally unfriendly catalysts and solvents. This work describes a multidisciplinary approach to the rapid establishment of biocatalytic routes to chiral aminodiols taking the original synthesis of (2S,3S)-2-aminopentane-1,3-diol as a specific example. An engineered variant of Escherichi coli transketolase (D469T) was used for the initial asymmetric ynthesis of (3S)-1,3-dihydroxypentan-2-one from the achiral substrates propanal and hydroxypyruvate. A bioinformatics led strategy was then used to identify and clone an omega-transaminase from Chromobacterium violaceum (DSM30191.) capable of converting the product of the transketolase-catalysed step to the required (2S,3S)-2-aminopentane-1,3-diol using isopropylamine as an inexpensive amine donor. Experiments; to characterize, optimize and model the kinetics of each reaction step were performed at the 1 mL scale using previously established automated microwell processing techniques. The microwell results, provided excellent predictions of the reaction kinetics when the. bioconversions were subsequently scaled up to preparative scales in batch stirred-tank reactors. The microwell methods thus provide process chemists and engineers with a valuable tool for the rapid and early evaluation of potential synthetic strategies. Overall, this work describes a concise and efficient biocatalytic route to chiral amino alcohols and illustrates an integrated multidisciplinary approach to bioconversion process design and scale-up.
• Towards a Mechanistic Understanding of Factors Controlling the Stereoselectivity of Transketolase
  作者：Anna Baierl、Axel Theorell、Ursula Mackfeld、Philipp Marquardt、Friederike Hoffmann、Stephanie Moers、Katharina Nöh、Patrick C. F. Buchholz、Jürgen Pleiss、Martina Pohl

  DOI：10.1002/cctc.201800299

  日期：2018.6.21

  relevant amino acids of TKs from different species, a standard numbering scheme was developed. Using this concept, H26, H261, and F434 were identified as the key residues which mediate stereoselectivity, where two main factors influenced the arrangement of ThDP‐bound donor and acceptor prior to carboligation: the relative orientation of the substrate side chains and the orientation of the acceptor carbonyl

  建立了硫胺二磷酸（ThDP）依赖性转酮酶（TK）的结构模型，以分析氨基酸交换对这种重要合成酶的立体选择性的影响。在这项研究中，研究了3-羟基丙酮酸作为供体和丙醛以及戊醛的碳结。基于文献数据和使用大肠杆菌的其他诱变研究TK是一种四态模型，旨在通过在形成CC键之前在活性位点中供体和受体底物的相对取向来解释TK的立体选择性。为了能够对不同物种的TK的相关氨基酸进行功能比较，开发了一种标准的编号方案。使用这个概念，H26，H261和F434被确定为介导立体选择性的关键残基，其中两个主要因素影响碳键化之前ThDP结合的供体和受体的排列：底物侧链的相对方向和受体羰基朝向供体羟基。该模型提供了第一个框架，用于了解传统知识与立体选择性之间的结构-功能关系。