3-Hydroxy-3-Carboxy-Adipic Acid | 13052-73-8

• 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: 3-Hydroxy-3-Carboxy-Adipic Acid
• 英文别名: (2R)-2-hydroxybutane-1,2,4-tricarboxylic acid
• CAS: 13052-73-8
• 化学式: C₇H₁₀O₇
• 分子量: 206.152
• InChiKey: XKJVEVRQMLKSMO-SSDOTTSWSA-N

物化性质

• 物理描述：
  Solid
• 碰撞截面：
  145 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -1.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-Hydroxy-3-Carboxy-Adipic Acid 在 盐酸 、 水 作用下， 生成 (+)-Homocitric acid lactone
  参考文献：
  名称：

  3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: an approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

  摘要：

  Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methylalkoxycarbonyl- and 3(2-Boc-aminoethyl)-alkoxycarbonyl-1,2-cyclopentanediones homocitric and lycoperdic acid precursors. Homocitric and lycoperdic acids were synthesized using asymmetric oxidation with the Ti(OiPr)(4)/tartaric ester/tBuOOH complex in two steps from the obtained precursors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.014
• 作为产物：
  描述：

  环辛烷-1,2-二酮 在 咪唑 、 titanium(IV) isopropylate 、 叔丁基过氧化氢 、 N-溴代丁二酰亚胺(NBS) 、 三甲基氯硅烷 、 L-(+)-酒石酸二乙酯 、 四丁基氟化铵 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 65.17h， 生成 3-Hydroxy-3-Carboxy-Adipic Acid
  参考文献：
  名称：

  3-Alkyl-1,2-cyclopentanediones by Negishi cross-coupling of a 3-bromo-1,2-cyclopentanedione silyl enol ether with alkylzinc reagents: an approach to 2-substituted carboxylic acid γ-lactones, homocitric and lycoperdic acids

  摘要：

  Negishi cross-coupling of the silyl-protected 3-bromoenol of 1,2-cyclopentanedione with primary and secondary alkylzinc reagents using Pd-catalysts affords 3-alkyl substituted 1,2-cyclopentanediones in good yield. The method was applied to obtain 3-methylalkoxycarbonyl- and 3(2-Boc-aminoethyl)-alkoxycarbonyl-1,2-cyclopentanediones homocitric and lycoperdic acid precursors. Homocitric and lycoperdic acids were synthesized using asymmetric oxidation with the Ti(OiPr)(4)/tartaric ester/tBuOOH complex in two steps from the obtained precursors. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.10.014

文献信息

• ALTERNATIVE PATHWAYS TO ADIPIC ACID BY COMBINED FERMENTATION AND CATALYTIC METHODS
  申请人：BioAmber Inc.

  公开号：US20150225329A1

  公开（公告）日：2015-08-13

  Processes process for producing adipate or adipic acid using biological pathways and chemical catalyzes are disclosed. Homocitric acid may be a substrate in reaction pathways leading to adipic acid or a salt thereof.

  揭示了利用生物途径和化学催化剂生产己二酸盐或己二酸的过程。顺己二酸可能是通向己二酸或其盐的反应途径中的底物。
• 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。
• Biological Synthesis of Difunctional Alkanes from Carbohydrate Feedstocks
  申请人：Baynes Brian M.

  公开号：US20110171696A1

  公开（公告）日：2011-07-14

  Aspects of the invention relate to methods for the production of difunctional alkanes in host cells. In particular, aspects of the invention describe components of genes associated with the difunctional alkane production from carbohydrate feedstocks in host cells. More specifically, aspects of the invention describe metabolic pathways for the production of adipic acid, aminocaproic acid, caprolactam, and hexamethylenediamine via 2-ketopimelic acid.

  本发明涉及在宿主细胞中生产双官能基烷烃的方法。具体而言，本发明描述了与从碳水化合物饲料在宿主细胞中生产双官能基烷烃相关的基因组成部分。更具体地，本发明描述了通过2-酮基戊二酸生产己二酸、氨基己酸、己内酰胺和六亚甲基二胺的代谢途径。
• BIOLOGICAL SYNTHESIS OF DIFUNCTIONAL ALKANES FROM CARBOHYDRATE FEEDSTOCKS
  申请人：Baynes Brian M.

  公开号：US20120164702A1

  公开（公告）日：2012-06-28

  Aspects of the invention relate to methods for the production of difunctional alkanes in host cells. In particular, aspects of the invention describe components of genes associated with the difunctional alkane production from carbohydrate feedstocks in host cells. More specifically, aspects of the invention describe metabolic pathways for the production of adipic acid, aminocaproic acid, caprolactam, and hexamethylenediamine via 2-ketopimelic acid.

  本发明涉及在宿主细胞中生产双官能基烷烃的方法。具体而言，本发明描述了与从碳水化合物饲料中在宿主细胞中生产双官能基烷烃相关的基因组成部分。更具体地，本发明描述了通过2-酮基戊二酸生产己二酸、氨基己酸、己内酰胺和六亚甲基二胺的代谢途径。
• BIOLOGICAL SYNTHESIS OF DIFUNCTIONAL ALKANES FROM ALPHA KETOACIDS
  申请人：Celexion, Llc

  公开号：EP2366026A2

  公开（公告）日：2011-09-21