mono(1-phenylethyl) pentanedioate | 130468-88-1

• 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: mono(1-phenylethyl) pentanedioate
• 英文别名: 4-((1-phenylethoxy)carbonyl)butanoic acid；5-Oxo-5-(1-phenylethoxy)pentanoic acid
• CAS: 130468-88-1
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: ZFFMPFVNLVZLMM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  mono(1-phenylethyl) pentanedioate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 immobilized Candida antarctica Lipase B 、 水 作用下， 以 二氯甲烷 、 正己烷 为溶剂， 反应 24.0h， 以17.7 mg的产率得到(R)-(+)-1-苯基乙醇
  参考文献：
  名称：

  酶介导的可溶性聚合物负载的羧酸盐的对映选择性水解

  摘要：

  公开了酶介导的水溶性聚合物负载的羧酸盐的对映选择性水解。通过将（±）-1-苯基乙醇通过带有琥珀酸酯间隔基的羧酸酯连接基固定在改性的MPEG（MPEG / NH 2）上，合成了代表性的由单甲氧基聚（乙二醇）（MPEG，av MW 5000）支撑的底物。对于水解酶的筛选，将基板对映选择性脂肪酶水解从南极假丝酵母中的混合溶剂（诺维信435）（己烷/缓冲液= 9/1）在30℃下，得到剩余的（小号） -底物和生成的（R）-醇（E值> 200）。无需任何费力的柱色谱，即可通过简单的步骤轻松分离产物。用NaOH的MeOH / H 2 O溶液水解底物，得到相应的（S）-醇。我们还发现，在MPEG部分和羧酸酯连接基之间的间隔基结构强烈地影响了反应性和对映选择性，带有谷氨酸间隔基的底物给出了最好的结果。我们的程序适用于几种旋光性醇的制备。

  DOI：

  10.1016/j.tet.2010.07.076
• 作为产物：
  描述：

  戊二酸酐 、 苏合香醇 在 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 生成 mono(1-phenylethyl) pentanedioate
  参考文献：
  名称：

  酶介导的二羧酸单酯的对映选择性水解

  摘要：

  研究了酶介导的二羧酸单酯的高对映选择性水解。通过将相应的醇与二羧酸酐偶联制备的外消旋底物在30°C的缓冲液中被南极假丝酵母（Novozym 435）的脂肪酶对映体选择性水解。可以通过简单的提取方法容易地分离产物，而无需费力的柱色谱，得到两种醇的对映异构体。然后，我们确定二羧酸单酯是制备光学活性醇的合适替代底物。

  DOI：

  10.2174/157017812803521108

文献信息

• Glutaryl Acylases: One-Reaction Enzymes or Versatile Enantioselective Biocatalysts?
  作者：Stefano Raimondi、Daniela Monti、Ugo Maria Pagnoni、Sergio Riva

  DOI：10.1002/adsc.200303013

  日期：2003.6

  A significant broad substrate specificity, that crosses over the usual β-lactam derivatives, has been observed with an industrial glutaryl-7-aminocephalosporanic acid acylase (GA). This enzyme possesses significant enantioselective amidase and even esterase activity, with a stereopreference for the S-enantiomer. The easy separation of products from unreacted reagents, possessing different physical-chemical

  用工业戊二酰-7-氨基头孢烷酸酰基转移酶（GA）已观察到跨越常规β-内酰胺衍生物的显着广泛的底物特异性。该酶具有显着的对映选择性酰胺酶和甚至酯酶活性，并具有S-对映异构体的立体偏好。通过溶剂萃取，避免在反应后处理过程中避免色谱或蒸馏，可以轻松地将具有不同物理化学性质的产物与未反应的试剂分离。
• Enantioselective esterase activity of an industrial glutaryl acylase
  作者：Sara Adani、Stefano Raimondi、Luca Forti、Daniela Monti、Sergio Riva

  DOI：10.1016/j.tetasy.2005.06.024

  日期：2005.7

  The unexpected esterase activity of an industrial glutaryl acylase was investigated. Glutaryl esters of a series of primary and secondary alcohols as well as of phenols were all efficiently hydrolyzed, the only exception being the sterically hindered glutarate of thymol. The enantioselectivities of the acylase, which were evaluated with three of these substrates, were quite low (E values ranging between 1.9 and 7.2), but were significantly improved by substrate and/or solvent engineering. Enantiomerically enriched hydrolyzed alcohols and unreacted glutarates can be easily separated by selective extraction, thus avoiding chromatographic steps. (C) 2005 Elsevier Ltd. All rights reserved.
• Catalytic antibodies with acyl-transfer capabilities: mechanistic and kinetic investigations
  作者：Kim D. Janda、Jon A. Ashley、Teresa M. Jones、Donald A. McLeod、Diane M. Schloeder、Michael I. Weinhouse、Richard A. Lerner、Richard A. Gibbs、Patricia A. Benkovic

  DOI：10.1021/ja00001a042

  日期：1991.1

  Antibodies have been shown to catalyze acyl-transfer reactions. The processes by which they perform such tasks have often been postulated but largely remain unknown. An extended study is presented on three different monoclonal antibodies that catalyze the hydrolysis of an alkyl ester and an aryl amide bond. Antibodies 2H6 and 21H3 catalyze the hydrolysis of an unactivated benzyl ester and show exquisite specificity for substrates with either the R or S configuration, respectively, while 43C9 catalyzes the cleavage of a p-nitroanilide amide bond. New substrates were synthesized and buffer-assisted reactions were employed to determine antibody-substrate fidelity. Oxygen-18 incorporation experiments were performed providing evidence that these antibody-mediated reactions proceed through attack at the acyl carbonyl, and excluding the possibility of an S(N)2 displacement; mechanism for the ester hydrolysis reaction. A ph-rate profile study in protium and deuterium oxide was performed on antibody 43C9. This revealed an apparent PK(a) of approximately 9 involved in catalysis, but both the presence and absence of a solvent isotope effect in the ph-dependent and -independent regions suggested a multistep reaction pathway may be operative.
• JANDA, KIM D.;ASHLEY, JON A.;JONES, TERESA M.;MCLEOD, DONALD A.;SCHLOEDER+, J. AMER. CHEM. SOC., 113,(1991) N, C. 291-297
  作者：JANDA, KIM D.、ASHLEY, JON A.、JONES, TERESA M.、MCLEOD, DONALD A.、SCHLOEDER+

  DOI：——

  日期：——
• Enzyme-mediated enantioselective hydrolysis of soluble polymer-supported carboxylates
  作者：Masayuki Okudomi、Kanpei Ageishi、Tomomi Yamada、Naoka Chihara、Takuya Nakagawa、Katsumi Mizuochi、Kazutsugu Matsumoto

  DOI：10.1016/j.tet.2010.07.076

  日期：2010.10

  The enzyme-mediated enantioselective hydrolysis of water-soluble polymer-supported carboxylates is disclosed. The representative monomethoxy poly(ethylene glycol) (MPEG, av MW 5000)-supported substrate was synthesized by immobilization of (±)-1-phenylethanol onto the modified MPEG (MPEG/NH2) through an carboxylate linker with a succinate spacer. For the screening of the hydrolytic enzymes, the substrate

  公开了酶介导的水溶性聚合物负载的羧酸盐的对映选择性水解。通过将（±）-1-苯基乙醇通过带有琥珀酸酯间隔基的羧酸酯连接基固定在改性的MPEG（MPEG / NH 2）上，合成了代表性的由单甲氧基聚（乙二醇）（MPEG，av MW 5000）支撑的底物。对于水解酶的筛选，将基板对映选择性脂肪酶水解从南极假丝酵母中的混合溶剂（诺维信435）（己烷/缓冲液= 9/1）在30℃下，得到剩余的（小号） -底物和生成的（R）-醇（E值> 200）。无需任何费力的柱色谱，即可通过简单的步骤轻松分离产物。用NaOH的MeOH / H 2 O溶液水解底物，得到相应的（S）-醇。我们还发现，在MPEG部分和羧酸酯连接基之间的间隔基结构强烈地影响了反应性和对映选择性，带有谷氨酸间隔基的底物给出了最好的结果。我们的程序适用于几种旋光性醇的制备。