(S)-dimethyl 2-butyramidosuccinate

• 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)-dimethyl 2-butyramidosuccinate
• 英文别名: (R)-N-butanoyl dimethyl aspartate；dimethyl (2R)-2-(butanoylamino)butanedioate
• 化学式: C₁₀H₁₇NO₅
• 分子量: 231.249
• InChiKey: LCSJUAITIFGCJF-SSDOTTSWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  16
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  rac-dimethyl 2-butyramidosuccinate 在 acylase I from Aspergillus melleus 、 正丁醇 作用下， 反应 152.0h， 生成 (S)-dimethyl 2-butyramidosuccinate
  参考文献：
  名称：

  在有机溶剂中酶法制备对映体纯的苹果酸和天冬氨酸衍生物

  摘要：

  研究了通过高区域选择性脂肪酶和酰基转移酶I酶动力学分解苹果酸和天冬氨酸二酯及其N-丁酰基二甲基酯的动力学方法。硅藻土上的南极假丝酵母脂肪酶A催化了羟基和氨基的对映选择性酰化。来自米曲霉和南极假丝酵母脂肪酶B的酰化酶I分别催化酯基在α-和β-位的对映选择性醇化。

  DOI：

  10.1016/s0957-4166(99)00476-0

文献信息

• Stereo-Controlled Asymmetric Bioreduction of α,β-Dehydroamino Acid Derivatives
  作者：Clemens Stueckler、Christoph K. Winkler、Mélanie Hall、Bernhard Hauer、Melanie Bonnekessel、Klaus Zangger、Kurt Faber

  DOI：10.1002/adsc.201100042

  日期：2011.5.9

  α,β‐Dehydroamino acid derivatives proved to be a novel substrate class for ene‐reductases from the ‘old yellow enzyme’ (OYE) family. Whereas N‐acylamino substituents were tolerated in the α‐position, β‐analogues were generally unreactive. For aspartic acid derivatives, the stereochemical outcome of the bioreduction using OYE3 could be controlled by variation of the N‐acyl protective group to furnish

  事实证明，α，β-脱氢氨基酸衍生物是“老黄酶”（OYE）家族中烯类还原酶的新型底物类别。而N-酰氨基取代基是在α位的耐受性，β-类似物普遍不反应。对于天冬氨酸衍生物，使用OYE3进行生物还原的立体化学结果可通过改变N-酰基保护基来提供相应的（S）-或（R）-氨基酸衍生物来控制。立体偏爱的这种转变是通过交换活化酯基团来改变底物结合力来解释的，这已通过2 H标记实验得到了证明。
• 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。
• Enzymatic methods for the preparation of enantiopure malic and aspartic acid derivatives in organic solvents
  作者：Arto Liljeblad、Liisa T Kanerva

  DOI：10.1016/s0957-4166(99)00476-0

  日期：1999.11

  The kinetic resolution of malic and aspartic acid diesters as well as of its N-butanoyl dimethyl ester by highly regioselective lipases and acylase I enzymes were studied. Candida antarctica lipase A on Celite catalyzed the enantioselective acylation of the hydroxyl and amino groups. Acylase I from Aspergillus melleus and Candida antarctica lipase B catalyzed the enantioselective alcoholyses of the

  研究了通过高区域选择性脂肪酶和酰基转移酶I酶动力学分解苹果酸和天冬氨酸二酯及其N-丁酰基二甲基酯的动力学方法。硅藻土上的南极假丝酵母脂肪酶A催化了羟基和氨基的对映选择性酰化。来自米曲霉和南极假丝酵母脂肪酶B的酰化酶I分别催化酯基在α-和β-位的对映选择性醇化。