(3S)-1,3-dihydroxy-3-phenylpropan-2-one | 104208-69-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (3S)-1,3-dihydroxy-3-phenylpropan-2-one
• 英文别名: (S)-1,3-dihydroxy-1-phenylpropan-2-one；(S)-1,3-dihydroxy-1-phenyl-2-propanone；(1S)-1,3-dihydroxy-1-phenylpropan-2-one
• CAS: 104208-69-7
• 化学式: C₉H₁₀O₃
• 分子量: 166.177
• InChiKey: TWEAOVXYLNFDMZ-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  12
• 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：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,3,5-三苯基氯化四氮唑 、 (3S)-1,3-dihydroxy-3-phenylpropan-2-one 在 MP-carbonate resin 、 双甘肽 、 sodium hydroxide 作用下， 以 水 、 甲醇 为溶剂， 反应 17.03h， 生成 1-phenyl-3-hydroxy-1,2-propanedione 、 1,3,5-triphenylformazan
  参考文献：
  名称：

  A colorimetric assay for screening transketolase activity

  摘要：

  A tetrazolium red-based colorimetric assay has been devised to screen for transketolase activity with a range of aldehyde acceptors. The colorimetric TK assay is able to detect > 8% bioconversion using non-alpha-hydroxylated aldehydes as acceptor substrates and is significantly faster and more convenient to use than chromatographic procedures. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.06.008
• 作为产物：
  描述：

  3-羟基-2-氧代丙酸 、 苯甲醛 在 转酮醇酶 thiamine pyrophosphate 、 magnesium chloride 作用下， 以 水 为溶剂， 生成 (3S)-1,3-dihydroxy-3-phenylpropan-2-one
  参考文献：
  名称：

  Enzyme-catalyzed synthesis of carbohydrates: synthetic potential of transketolase

  摘要：

  The synthetic potential of yeast or spinach transketolases was studied, using hydroxypyruvate as a donor substrate and 31 aldehydes as acceptors. All of them react, including aromatic, heteroaromatic and alpha,beta unsaturated aldehydes.

  DOI：

  10.1016/s0040-4039(00)93434-8

文献信息

• METHODS AND COMPOSITIONS FOR PREVENTING OPIOID ABUSE
  申请人：Waterville Valley Technologies, Inc.

  公开号：US20160326182A1

  公开（公告）日：2016-11-10

  Abuse-resistant opioid compounds, drug delivery systems, pharmaceutical compositions comprising an opioid covalently bound to a chemical moiety are provided. Methods of delivering an active ingredient to a subject and methods of preventing opioid abuse are also provided.

  提供了耐滥用的阿片类化合物、药物输送系统、含有阿片类药物与化学基团共价结合的制药组合物。还提供了将活性成分输送给受试者的方法以及预防阿片类药物滥用的方法。
• α,α′-Dihydroxyketone formation using aromatic and heteroaromatic aldehydes with evolved transketolase enzymes
  作者：James L. Galman、David Steadman、Sarah Bacon、Phattaraporn Morris、Mark E. B. Smith、John M. Ward、Paul A. Dalby、Helen C. Hailes

  DOI：10.1039/c0cc02911d

  日期：——

  Transketolase mutants have been identified that accept aromatic acceptors with good stereoselectivities, in particular benzaldehyde for which the wild type enzyme showed no activity.

  已鉴定出转酮醇酶突变体，这些突变体能够以良好的立体选择性接受芳香族受体，特别是苯甲醛，而野生型酶对此无活性。
• Engineering a thermostable transketolase for arylated substrates
  作者：Thangavelu Saravanan、Marie-Luise Reif、Dong Yi、Marion Lorillière、Franck Charmantray、Laurence Hecquet、Wolf-Dieter Fessner

  DOI：10.1039/c6gc02017h

  日期：——

  Transketolase variants were engineered to utilize arylalkanals and benzaldehyde as substrates with up to 28-fold rate acceleration for C–C bond formation with good yields (50–73%) and virtually complete (3S)-stereoselectivity (>99% ee).

  转酮酶变种被工程化以利用芳基烷醛和苯甲醛作为底物，可实现C-C键形成高达28倍的速率加速，且产率良好（50-73%），并且具有几乎完全的（3S）立体选择性（>99% ee）。
• Investigating the reaction mechanism and organocatalytic synthesis of α,α′-dihydroxy ketones
  作者：James L. Galman、David Steadman、Lisa D. Haigh、Helen C. Hailes

  DOI：10.1039/c2ob06939c

  日期：——

  biomimetic TK one-pot reaction using hydroxypyruvate and aldehydes to generate α,α′-dihydroxy ketones in water has recently been described. To investigate this tertiary-amine mediated reaction mechanism two approaches were used. Firstly, 13C labelled lithium hydroxypyruvate was synthesised and used to establish where hydroxypyruvate is incorporated in the product. In separate experiments reaction intermediates

  使用羟基丙酮酸和醛类药物进行仿生TK一锅反应，以生成α，α'-二羟基酮 水最近已有描述。为了研究这种叔胺介导的反应机理，使用了两种方法。首先，标有13 C羟基丙酮酸锂合成并用于确定在产品中掺入羟基丙酮酸的位置。在单独的实验中，还使用串联质谱ESI-MS / MS的ESI-MS成功拦截了反应中间体并在结构上进行了鉴定。这些研究表明，似乎有两种机理在起作用，一种涉及将叔胺催化剂添加到羟基丙酮酸中，另一种涉及基于醇醛的机理。由于第一种机理可以通过向醛中添加中间体来实现面部立体分化，因此对使用手性催化剂进行了初步研究，并首次在水性介质中实现了α，α'-二羟基酮的首次不对称有机催化合成。使用奎宁醚催化剂，得到50％ee。
• Enzyme-catalyzed synthesis of carbohydrates: synthetic potential of transketolase
  作者：Colette Demuynck、Jean Bolte、Laurence Hecquet、Valérie Dalmas

  DOI：10.1016/s0040-4039(00)93434-8

  日期：1991.9

  The synthetic potential of yeast or spinach transketolases was studied, using hydroxypyruvate as a donor substrate and 31 aldehydes as acceptors. All of them react, including aromatic, heteroaromatic and alpha,beta unsaturated aldehydes.