(S)-3-Aminovaleric acid ethyl ester | 470707-09-6

• 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: (S)-3-Aminovaleric acid ethyl ester
• 英文别名: ethyl (3S)-3-aminopentanoate
• CAS: 470707-09-6
• 化学式: C₇H₁₅NO₂
• 分子量: 145.202
• InChiKey: OKIYALVMFMZSLV-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  10
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基戊酸 在 Candida antarctica lipase B 、 氯化亚砜 作用下， 反应 0.75h， 生成 (S)-3-Aminovaleric acid ethyl ester
  参考文献：
  名称：

  Structural effects on chemo- and enantioselectivity of Candida antarctica lipase B - Resolution of β-amino esters

  摘要：

  用Candida antarctica脂肪酶B催化的五种β-氨基酯与纯正丁基丁酸酯以及二异丙基醚中2,2,2-三氟乙基丁酸酯的反应进行了研究，同时还研究了相同β-氨基酯及其N-丁酰胺与纯正丁醇的反应。随着底物从乙基3-氨基丁酸酯（1a）增大到戊酸酯（1b）或更大，底物的氨基和酯基与不对称丁酸酯同时反应的连续分辨可能性逐渐降低。另一方面，N-酰化的β-氨基酯在丁醇中成功进行了醇解，E > 100。进行了N-丁酰化1a的克级分辨，以展示该方法的实用性。关键词：脂肪酶，酯交换，酰化，醇解，分辨，β-氨基酯。

  DOI：

  10.1139/v02-015

文献信息

• Stereoselective ring opening of chiral oxazolidines by reformatsky reagents: an enantioselective entry to β-amino esters.
  作者：Celia Andrés、Alfonso González、Rafael Pedrosa、Alfonso Pérez-Encabo

  DOI：10.1016/s0040-4039(00)78889-7

  日期：1992.5

  Chiral oxazolidines obtained by condensation of aldehydes with (-).(R)- or (+).(S)-N-benzylphenylglycinol react with the Reformatsky reagent derived from ethyl bromoacetate, in mild reaction conditions (Et2O or CH2Cl2, 0°C, 15-60 min), leading to ethyl β-amino carboxylates in moderate to good diastereomeric excess (60-92%). These ring opening products are transformed into primary β-aminoesters, in

  通过醛与（-）。（R）-或（+）。（S）-N-苄基苯基甘氨醇缩合获得的手性恶唑烷在温和的反应条件下（Et 2 O或CH 2 Cl 2，0℃，15-60分钟），从而导致乙基β-氨基羧酸盐在中度至良好的非对映体过量（60-92％）。通过在碳上用H 2 / Pd脱苄基化，一步就将这些开环产物转变成伯β-氨基酯。以此方式，可以两种对映体形式获得β-氨基羧酸乙酯，化学收率范围为55-76％和中等至良好的ee（60-92％）。
• Improving Catalytic Activity and Reversing Enantio‐Specificity of ω‐Transaminase by Semi‐Rational Engineering en Route to Chiral Bulky β‐Amino Esters
  作者：Yingang Wang、Jinhui Feng、Wenyue Dong、Xi Chen、Peiyuan Yao、Qiaqing Wu、Dunming Zhu

  DOI：10.1002/cctc.202100503

  日期：2021.8.6

  exhibited activity toward bulky β-keto esters. Furthermore, a substrate-dependent shift in enantio-preference of HBV variant towards β-keto esters with linear or branched aliphatic substituents was observed. The best variant was applied to the asymmetric synthesis of aliphatic β-amino acids at semi-preparative scale with high yield and enantioselectivity. This study will improve the general understanding

  野生型 ω-转氨酶的应用受到对庞大底物的空间位阻的限制，因此提高对具有两个与羰基相邻的庞大取代基的底物的催化效率和立体选择性具有普遍意义。在本研究中，根据双底物结合口袋理论，一种来自越南伯克霍尔德菌的 ( S )-选择性 ω-转氨酶G4 对具有小空间位阻的 β-酮酯显示出微弱的催化活性，被设计为接受任何野生型酶都无法获得的大体积 β-酮酯。获得了一些所需的变体，它们对庞大的 β-酮酯表现出活性。此外，观察到 HBV 变体的对映体偏好向具有线性或支化脂肪族取代基的 β-酮酯的底物依赖性转变。最好的变体以高产率和对映选择性应用于半制备规模的脂肪族 β-氨基酸的不对称合成。这项研究将提高一般理解并激发进一步的工程工作，以逆转 ω-转氨酶的对映特异性。
• Substrate profile of an ω-transaminase from Burkholderia vietnamiensis and its potential for the production of optically pure amines and unnatural amino acids
  作者：Jinju Jiang、Xi Chen、Jinhui Feng、Qiaqing Wu、Dunming Zhu

  DOI：10.1016/j.molcatb.2013.11.013

  日期：2014.2

  A new (S)-enantioselective omega-transaminase (omega-TA) gene from Burkholderia vietnamiensis G4 was functionally expressed in Escherichia coli BL21 (DE3), and the purified recombinant N-terminal His-tagged (omega-TA (HBV-omega-TA) had a dimeric structure with optimum pH and temperature of 8.4 and 40 degrees C, respectively. The enzyme showed higher activities toward aromatic amines than aliphatic amines and (S)-1-methylbenzylamine ((S)-alpha-MBA) was the most active amino donor. For amino acceptor, keto acids, keto esters and aldehydes were more reactive than ketones with pyruvate ethyl ester being most active. Several chiral amines and unnatural amino acids or esters were synthesized using HBV-w-TA as the catalyst and isopropylamine or (S)-alpha-MBA as amino donor. Notably, HBV-omega-TA catalyzed the amino transfer to beta-keto esters to give optically pure beta-amino acid esters. In addition, glyoxylate was used as amino acceptor for the first time in the kinetic resolution of racemic amines and optically pure amines, such as (R)-1-methylbenzylamine, (R)-1-phenylpropylamine, (R)-2-amino-4-phenylbutane and (R)-1-aminotetraline, were obtained. (C) 2013 Elsevier B.V. All rights reserved.
• Structural effects on chemo- and enantioselectivity of <i>Candida antarctica</i> lipase B - Resolution of β-amino esters
  作者：Szilvia Gedey、Arto Liljeblad、László Lázár、Ferenc Fülöp、Liisa T Kanerva

  DOI：10.1139/v02-015

  日期：2002.6.1

  The Candida antarctica lipase B-catalyzed reactions of five β-amino esters with neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied, as were the reactions of the same β-amino esters and their N-butanamides with neat butanol. The possibility for sequential resolution, where the amino and ester functions of the substrate both react with an achiral butanoate, became less likely with increasing size of the substrate from ethyl 3-aminobutanoate (1a) to pentanoate (1b) or larger. On the other hand, the alcoholyses of N-acylated β-amino esters successfully proceeded in butanol with E > 100. Gram-scale resolution of the N-butanoylated 1a was performed to demonstrate the usefulness of the method. Key words: lipase, interesterification, acylation, alcoholysis, resolution, β-amino esters.

  用Candida antarctica脂肪酶B催化的五种β-氨基酯与纯正丁基丁酸酯以及二异丙基醚中2,2,2-三氟乙基丁酸酯的反应进行了研究，同时还研究了相同β-氨基酯及其N-丁酰胺与纯正丁醇的反应。随着底物从乙基3-氨基丁酸酯（1a）增大到戊酸酯（1b）或更大，底物的氨基和酯基与不对称丁酸酯同时反应的连续分辨可能性逐渐降低。另一方面，N-酰化的β-氨基酯在丁醇中成功进行了醇解，E > 100。进行了N-丁酰化1a的克级分辨，以展示该方法的实用性。关键词：脂肪酶，酯交换，酰化，醇解，分辨，β-氨基酯。