ethyl (S)-3-butanamidobutanate

• 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: ethyl (S)-3-butanamidobutanate
• 英文别名: ethyl (3S)-3-(butanoylamino)butanoate
• 化学式: C₁₀H₁₉NO₃
• 分子量: 201.266
• InChiKey: YUQFVSKGTHLMON-QMMMGPOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氨基丁酸乙酯 在 Candida antarctica lipase B 、 三乙胺 作用下， 反应 1.5h， 生成 ethyl (S)-3-butanamidobutanate
  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

• Formation and hydrolysis of amide bonds by lipase A from Candida antarctica; exceptional features
  作者：Arto Liljeblad、Pauli Kallio、Marita Vainio、Jarmo Niemi、Liisa T. Kanerva

  DOI：10.1039/b920939p

  日期：——

  studied for their ability to catalyze the hydrolysis of amide bonds in N-acylated α-amino acids, 3-butanamidobutanoic acid (β-amino acid) and its ethyl ester. The activity toward amide bonds is highly untypical of lipases, despite the close mechanistic analogy to amidases which normally catalyze the corresponding reactions. Most CAL-A preparations cleaved amide bonds of various substrates with high enantioselectivity

  研究了南极假丝酵母（CAL-A）的各种商业化冻干和固定化脂肪酶A的制备方法，它们具有催化N-酰化α-氨基酸中酰胺键水解的能力，3-丁酰胺基丁酸 （β-氨基酸）及其乙酯。尽管对酰胺酶的机制与通常催化相应反应的酰胺酶非常相似，但对脂肪酶的酰胺键活性却是非常不典型的。最多CAL-A尽管检测到底物选择性和催化速率变化很大，但这些制剂仍具有高对映选择性地裂解了各种底物的酰胺键。通过分馏和分析商业冻干制备的蛋白质，研究了污染物蛋白种类对这些键的水解活性的可能作用。CAL-A（Cat＃ICR-112，Codexis）。除了少量杂质外，还检测到两个同样丰富的蛋白质，它们在SDS-PAGE上以计算出的CAL-A大小相距几kDa的距离迁移。基于肽片段分析和序列比较，两个条带均与CAL-A共享大量的序列覆盖范围。然而，在较小的片段中未鉴定出被称为活动位点皮瓣的构成运动结构域的C末端肽。两种形式的分离的凝胶过滤部分CAL-A
• Sequential resolution of ethyl 3-aminobutyrate with carboxylic acid esters by Candida antarctica lipase B
  作者：Szilvia Gedey、Arto Liljeblad、Ferenc Fülöp、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(99)00261-x

  日期：1999.7

  The reactions of ethyl 3-aminobutyrate 1 with carboxylic acid esters, catalyzed by lipases from Candida antarctica, Pseudomonas cepacia and Pseudomonas fluorescens, have been studied. The reactions take place on the amino and ester functions of the substrate provided that the alkyl group of the achiral ester differs from ethyl. This property has been exploited for the Candida antarctica lipase B-catalyzed resolution of 1 in butyl butyrate, leading to the unreacted enantiomer (S)-1 and butyl 3-aminobutyrate, and to the butanamide of butyl (R)-3-aminobutyrate, (C) 1999 Elsevier Science Ltd. All rights reserved.
• Preparation of highly enantiopure β-amino esters by Candida antarctica lipase A
  作者：Szilvia Gedey、Arto Liljeblad、László Lázár、Ferenc Fülöp、Liisa T. Kanerva

  DOI：10.1016/s0957-4166(01)00002-7

  日期：2001.2

  The enantioselectivities for the reactions of aliphatic beta -substituted beta -amino esters [RCH(NH2)CH2CO2Et with R = Me, Et, n-Pr, i-Pr, CHEt2, cyclohexyl and Ph] with butyl butanoate in neat butyl butanoate and with 2,2,2-trifluoroethyl butanoate in diisopropyl ether were studied in the presence of Candida antarctica lipase A. Enantioselectivities ranging from good (E=70-100) to excellent (E>100) were commonly observed, allowing gram-scale resolution of the substrates. (C) 2001 Elsevier Science Ltd. 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。