(S)-2-羟基-2-(异丙基)琥珀酸 | 49601-06-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 中文名称: (S)-2-羟基-2-(异丙基)琥珀酸
• 英文名称: 2-Isopropylaepfelsaeure
• 英文别名: (2S)-2-Isopropylmalate；(2S)-2-hydroxy-2-propan-2-ylbutanedioic acid
• CAS: 49601-06-1
• 化学式: C₇H₁₂O₅
• 分子量: 176.169
• InChiKey: BITYXLXUCSKTJS-ZETCQYMHSA-N

物化性质

• 物理描述：
  Solid
• 熔点：
  144-146°C

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-氧代-3-甲基丁酸 、 alkaline earth salt of/the/ methylsulfuric acid 在 α-isopropylmalate synthase 作用下， 生成 (S)-2-羟基-2-(异丙基)琥珀酸
  参考文献：
  名称：

  The C-terminal regulatory domain is required for catalysis by Neisseria meningitidis α-isopropylmalate synthase

  摘要：

  alpha-Isopropylmalate synthase (alpha-IPMS) catalyses the first committed step in leucine biosynthesis in many pathogenic bacteria, including Neisseria meningitidis. This enzyme (NmelPMS) has been purified, characterised, and compared to alpha-IPMS proteins from other bacteria. NmeIPMS is a homodimer which catalyses the condensation of alpha-ketoisovalerate (alpha-KIV) and acetyl coenzyme A (AcCoA), and is inhibited by leucine. NmeIPMS can use altemate alpha-ketoacids as substrates and, in contrast to alpha-IPMS from other sources, is activated by a range of metal ions including Cd2+ and Zn2+ that have previously been reported as inhibitory, since they suppress the dithiodipyridone assay system rather than the enzyme itself Previous studies indicate that alpha-IPMS is a TIM barrel enzyme with an allosteric leucine-binding domain. To assess the importance of this domain, a truncated form of NmeIPMS was generated and characterised. Loss of the regulatory domain resulted in a loss of the ability to catalyse the aldol reaction, although the enzyme was still able to slowly hydrolyse AcCoA independently of alpha-KIV at a rate similar to that of the WT enzyme. This implies that the regulatory domain is not only required for control of enzymatic activity but may assist in the positioning of key residues in the catalytic TIM barrel. The importance of this domain to catalytic function may offer new strategies for inhibitor design. (C) 2010 Elsevier Inc. All rights reserved.

  DOI：

  10.1016/j.bbrc.2010.01.114

文献信息

• Method for the enzymatic production of 3-hydroxy-3-methylbutyric acid from acetone and acetyl-CoA
  申请人：Scientist of Fortune S.A.

  公开号：EP2940141A1

  公开（公告）日：2015-11-04

  Described is a method for the production of 3-hydroxy-3-methylbutyric acid (also referred to as beta-hydroxyisovalerate or HIV) from acetone and a compound which provides an activated acetyl group comprising the enzymatic conversion of acetone and a compound which provides an activated acetyl group into 3-hydroxy-3-methylbutyric acid. The conversion makes use of an enzyme which is capable of catalyzing the formation of a covalent bond between the carbon atom of the oxo (i.e. the C=O) group of acetone and the methyl group of the compound which provides an activated acetyl group. Preferably, the enzyme employed in the process is an enzyme with the activity of a HMG CoA synthase (EC 2.3.3.10) and/or a PksG protein and/or an enzyme with the activity of a C-C bond cleavage/condensation lyase, such as a HMG CoA lyase (EC 4.1.3.4). Also described are organisms which are able to produce 3-hydroxy-3-methylbutyric acid from acetone, a compound which provides an activated acetyl group, the use of the above-mentioned enzymes and organisms for the production of 3-hydroxy-3-methylbutyric acid as well as the use of acetone for the production of 3-hydroxy-3-methylbutyric acid.

  本方法涉及从丙酮和提供活化乙酰基的化合物中生产3-羟基-3-甲基丁酸（也称为β-羟基异戊酸或HIV）的方法，包括将丙酮和提供活化乙酰基的化合物经酶催化转化为3-羟基-3-甲基丁酸。转化利用一种能够催化丙酮的羰基（即C=O）基团的碳原子和提供活化乙酰基的化合物的甲基团之间形成共价键的酶。最好采用的酶是具有HMG CoA合成酶（EC 2.3.3.10）和/或PksG蛋白质活性以及C-C键裂解/缩合裂解酶活性（例如HMG CoA裂解酶（EC 4.1.3.4））的酶。本方法还涉及能够从丙酮和提供活化乙酰基的化合物中产生3-羟基-3-甲基丁酸的生物体，以及上述酶和生物体用于生产3-羟基-3-甲基丁酸的用途，以及丙酮用于生产3-羟基-3-甲基丁酸的用途。
• Plasmid vectors for eukaryotic cells and method for selecting transfected eukaryotic cells
  申请人：F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft

  公开号：EP0054223A2

  公开（公告）日：1982-06-23

  Improved vectors for screening eukaryotic transformants containing heterologous genes. The vectors comprise plasmids containing an insert consisting of a gene coding for an enzyme needed to produce an essential amino acid linked to multiple polyoma virus genes. By growing the transformant eukaryotic cells in a medium missing the essential amino acid corresponding to the vector gene and providing the precursor intermediate in the medium it is possible to screen for cells containing the vector.

  用于筛选含有异源基因的真核转化体的改良载体。 这些载体由质粒组成，质粒中含有一个插入物，该插入物由一个编码产生与多个多瘤病毒基因相连的必需氨基酸的酶的基因组成。 通过在缺少与载体基因相对应的必需氨基酸的培养基中培养转化真核细胞，并在培养基中提供前体中间体，可以筛选出含有载体的细胞。
• Fermentation process for production of alpha-isopropylmalic acid
  申请人：PFIZER INC.

  公开号：EP0095862A1

  公开（公告）日：1983-12-07

  A process for producing alpha-isopropylmalic acid by aerobically fermenting a new strain of Yarrowia lipolytica, namely ATCC 20628, and for recovering said acid from a fermentation medium. Also included is the said biologically pure strain and mutants thereof.

  一种通过有氧发酵一种新的脂肪溶解亚罗威氏菌株（即 ATCC 20628）来生产α-异丙基丙二酸，并从发酵培养基中回收所述酸的工艺。还包括上述生物纯菌株及其突变体。
• Probe compound for detecting and isolating enzymes and means and methods using the same
  申请人：Helmholtz-Zentrum für Infektionsforschung GmbH

  公开号：EP2230312A1

  公开（公告）日：2010-09-22

  The present invention relates to a probe compound that can comprise any substrate or metabolite of an enzymatic reaction in addition to an indicator component, such as, for example, a fluorescence dye, or the like. Moreover, the present invention relates to means for detecting enzymes in form of an array, which comprises any number of probe compounds of the invention which each comprise a different metabolite of interconnected metabolites representing the central pathways in all forms of life. Moreover, the present invention relates to a method for detecting enzymes involving the application of cell extracts or the like to the array of the invention which leads to reproducible enzymatic reactions with the substrates. These specific enzymatic reactions trigger the indicator (e.g. a fluorescence signal) and bind the enzymes to the respective cognate substrates. Moreover, the invention relates to means for isolating enzymes in form of nanoparticles coated with the probe compound of the invention. The immobilisation of the cognate substrates or metabolites on the surface of nanoparticles by means of the probe compounds allows capturing and isolating the respective enzyme, e.g. for subsequent sequencing.

  本发明涉及一种探针化合物，它可以包括酶反应的任何底物或代谢物，此外还包括指示成分，例如荧光染料或类似物。此外，本发明还涉及以阵列形式检测酶的方法，该阵列由任意数量的本发明探针化合物组成，每种探针化合物由代表所有生命形式中中心途径的相互关联的代谢物中的不同代谢物组成。此外，本发明还涉及一种检测酶的方法，该方法涉及将细胞提取物或类似物应用于本发明的阵列，从而导致与底物发生可重复的酶反应。这些特定的酶反应会触发指示剂（如荧光信号），并将酶与各自的同源底物结合。此外，本发明还涉及以涂覆有本发明探针化合物的纳米颗粒形式分离酶的方法。通过探针化合物将同源底物或代谢物固定在纳米颗粒表面，可以捕获和分离相应的酶，例如用于后续测序。
• Method for the enymatic production of 3-hydroxy-3-methylbutyric acid from acetone and acetyl-CoA
  申请人：Marliere, Philippe

  公开号：EP2295593A1

  公开（公告）日：2011-03-16

  Described is a method for the production of 3-hydroxy-3-methylbutyric acid (also referred to as beta-hydroxyisovalerate or HIV) from acetone and a compound which provides an activated acetyl group comprising the enzymatic conversion of acetone and a compound which provides an activated acetyl group into 3-hydroxy-3-methylbutyric acid. The conversion makes use of an enzyme which is capable of catalyzing the formation of a covalent bond between the carbon atom of the oxo (i.e. the C=O) group of acetone and the methyl group of the compound which provides an activated acetyl group. Preferably, the enzyme employed in the process is an enzyme with the activity of a HMG CoA synthase (EC 2.3.3.10) and/or a PksG protein and/or an enzyme with the activity of a C-C bond cleavage/condensation lyase, such as a HMG CoA lyase (EC 4.1.3.4). Also described are organisms which are able to produce 3-hydroxy-3-methylbutyric acid from acetone, a compound which provides an activated acetyl group, the use of the above-mentioned enzymes and organisms for the production of 3-hydroxy-3-methylbutyric acid as well as the use of acetone for the production of 3-hydroxy-3-methylbutyric acid.

  本发明描述了一种从丙酮和提供活化乙酰基的化合物生产 3-羟基-3-甲基丁酸（又称 β-羟基异戊酸或 HIV）的方法，包括用酶将丙酮和提供活化乙酰基的化合物转化为 3-羟基-3-甲基丁酸。这种转化使用一种酶，这种酶能够催化丙酮的氧代（即 C=O）基团的碳原子与提供活化乙酰基的化合物的甲基之间形成共价键。优选地，工艺中使用的酶是具有 HMG CoA 合成酶（EC 2.3.3.10）和/或 PksG 蛋白活性的酶和/或具有 C-C 键裂解/缩合裂解酶活性的酶，如 HMG CoA 裂解酶（EC 4.1.3.4）。还描述了能够从丙酮（一种提供活化乙酰基的化合物）中生产 3-羟基-3-甲基丁酸的生物、使用上述酶和生物生产 3-羟基-3-甲基丁酸以及使用丙酮生产 3-羟基-3-甲基丁酸。