4-hydroxy-4-methyl-2-ketoglutaric acid | 19071-44-4

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: 4-hydroxy-4-methyl-2-ketoglutaric acid
• 英文别名: 2-oxo-4-hydroxy-4-methylglutaric acid；4-hydroxy-4-methyl-2-oxoglutaric acid；parapyruvic acid；(R/S)-HMG；γ-methyl-γ-hydroxyl-α-keto-glutaric acid；HMOG；2-hydroxy-2-methyl-4-oxopentanedioic acid
• CAS: 19071-44-4
• 化学式: C₆H₈O₆
• 分子量: 176.126
• InChiKey: YRWAMSXHYBBHFL-UHFFFAOYSA-N

物化性质

• 沸点：
  406.1±35.0 °C(Predicted)
• 密度：
  1.579±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-hydroxy-4-methyl-2-ketoglutaric acid 在 bovine glutamic dehydrogenase 1,4-dihydronicotinamide adenine dinucleotide 、 L-谷氨酸 作用下， 以 phosphate buffer 为溶剂， 生成 (2S)-4-hydroxy-4-methylglutamic acid
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Glutamic Acid Analogues:  Substrate Specificity and Synthetic Applications of Branched Chain Aminotransferase from Escherichia coli

  摘要：

  [GRAPHICS]A new route to alpha-keto acids is described, based on the ozonolysis of enol acetates obtained from alpha-substituted beta-keto esters. Escherichia coli branched chain aminotransferase (BCAT) activity toward a variety of substituted 2-oxoglutaric acids was demonstrated analytically. BCAT was shown to have a broad substrate spectrum, complementary to that of aspartate aminotransferase, and to offer access to a variety of glutamic acid analogues. The usefulness of BCAT was demonstrated through the synthesis of several 3- and 4-substituted derivatives.

  DOI：

  10.1021/jo070805q
• 作为产物：
  描述：

  4-hydroxy-2-keto-4-methylglutaric lactone 在 水 作用下， 生成 4-hydroxy-4-methyl-2-ketoglutaric acid
  参考文献：
  名称：

  Montgomery et al., Journal of Biological Chemistry, 1956, vol. 221, p. 369,370

  摘要：

  DOI：

文献信息

• Methods And Systems For Increasing Production of Equilibrium Reactions
  申请人：Khare Bhagwan Anil

  公开号：US20080015361A1

  公开（公告）日：2008-01-17

  Methods and systems for increasing the production of equilibrium reactions are described. In some embodiments, a method comprises removing enzymes from a reaction mixture once equilibrium is achieved, selectively re-adding enzymes and reactants for driving the product-forming reaction to product, and optionally recycling stabilized intermediates, by-products and/or co-products back into the reaction mixture. In some embodiments, a method comprises purifying the desired product from a reaction mixture and selectively recycling one or more components of the reaction mixture, such as original reactants, intermediates, co-products or by-products back into the reaction mixture as desired to improve titer. Systems for implementing the methods are also provided. In some embodiments the methods and systems are implemented for increasing the production of monatin and monatin derivatives, produced in multi-step equilibrium pathways.

  描述了一种增加平衡反应产量的方法和系统。在某些实施例中，一种方法包括在达到平衡后从反应混合物中去除酶，选择性地重新添加酶和反应物以驱动生成产物的反应，并可选择性地将稳定的中间体、副产物和/或共产物循环回反应混合物。在某些实施例中，一种方法包括从反应混合物中纯化所需的产物，并选择性地将反应混合物中的一个或多个组分，如原始反应物、中间体、共产物或副产物循环回反应混合物，以提高产量。还提供了实施这些方法的系统。在某些实施例中，这些方法和系统被用于增加在多步平衡途径中产生的莫纳汀和莫纳汀衍生物的产量。
• Synthesis of 4,4-Disubstituted<scp>L</scp>-Glutamic Acids by Enzymatic Transamination
  作者：Virgil Hélaine、Joël Rossi、Thierry Gefflaut、Sébastien Alaux、Jean Bolte

  DOI：10.1002/1615-4169(200108)343:6/7<692::aid-adsc692>3.0.co;2-6

  日期：2001.8

  The syntheses of optically pure 4,4-dimethyl-L-glutamic acid as well as (2S,4R)- and (2S,4S)-4-hydroxy-4-methylglutamic acids have been achieved by transamination of the corresponding 2-oxo-4,4-dimethyl- and rac-2-oxo-4-hydroxy-4-methylglutaric acids using glutamic oxalacetic transaminase (GOT).

  光学纯的 4,4-二甲基-L-谷氨酸以及 (2S,4R)- 和 (2S,4S)-4-羟基-4-甲基谷氨酸的合成是通过相应的 2-氧代转氨基实现的-4,4-二甲基-和 rac-2-oxo-4-羟基-4-甲基戊二酸使用谷氨酸草酰乙酸转氨酶 (GOT)。
• Pyruvate ester composition and method of use for resuscitation after events of ischemia and reperfusion
  申请人：Xanthus Life Sciences, Inc.

  公开号：US20030073743A1

  公开（公告）日：2003-04-17

  A therapeutic composition comprising an alkyl, aralkyl, alkoxyalkyl or carboxyalkyl ester of 2-ketoalkanoic acid and a component for inducing and stabilizing the enol resonance form of the ester at physiological pH values is disclosed. The composition of the invention further comprises a pharmceutically acceptable carier vehicle in which the enol resonance form of the ester is stabilized at physiological pH values. Formulations containing the compositions of the invention permit the successful use of 2-ketoalkanoic acid esters, e.g., pyruvic acid esters, to treat, e.g., ischemic events, shock, organ reanimation, resuscitation and other recognized pyruvate-effective treatments. The compositions of the inventions are also useful in a process for preserving organ parts, organs or limbs removed from a living mammal and in need of preservation, e.g., for later transplantation to an organ recipient.

  本发明公开了一种治疗性组合物，包括2-酮基脂肪酸的烷基、芳基烷基、烷氧基烷基或羧基烷基酯和诱导和稳定酯在生理pH值下的烯醇共振形式的成分。本发明的组合物还包括一种药学上可接受的载体，其中酯的烯醇共振形式在生理pH值下得到稳定。包含本发明组合物的配方允许成功地使用2-酮基脂肪酸酯，例如丙酮酸酯，用于治疗缺血事件、休克、器官复苏、复苏和其他已知的丙酮酸有效治疗。本发明的组合物也适用于保存从需要保存的活体哺乳动物中取出的器官部分、器官或肢体，例如，以后移植给器官受体。
• Polypeptides and biosynthetic pathways for the production of monatin and its precursors
  申请人：Abraham W. Timothy

  公开号：US20050244937A1

  公开（公告）日：2005-11-03

  Methods and compositions that can be used to make monatin from glucose, tryptophan, indole-3-lactic acid, indole-3-pyruvate, and 2-hydroxy 2-(indol-3-ylmethyl)-4-keto glutaric acid, are provided. Methods are also disclosed for produding the indole-3-pyruvate and 2-hydroxy 2-(indol-3-ylmethyl)-4-keto glutaric acid intermediates. Compositions provided include nucleic acid molecules, polypeptides, chemical structures, and cells. Methods include in vitro and in vivo processes, and the in vitro methods include chemical reactions.

  提供了从葡萄糖、色氨酸、吲哚-3-乳酸、吲哚-3-丙酮酸和2-羟基2-(吲哚-3-基甲基)-4-酮戊酸制备莫纳丁的方法和组合物。还公开了制备吲哚-3-丙酮酸和2-羟基2-(吲哚-3-基甲基)-4-酮戊酸中间体的方法。提供的组合物包括核酸分子、多肽、化学结构和细胞。方法包括体外和体内过程，其中体外方法包括化学反应。
• Beverage compositions comprising monatin and methods of making same
  申请人：Abraham W. Timothy

  公开号：US20050106305A1

  公开（公告）日：2005-05-19

  The present invention relates to novel beverage compositions comprising monatin and methods for making such compositions. The present invention also relates to beverage compositions comprising specific monatin stereoisomers, specific blends of monatin stereoisomers, and/or monatin produced via a biosynthetic pathway in vivo (e.g., inside cells) or in vitro.

  本发明涉及包含莫纳丁的新型饮料组合物及其制备方法。本发明还涉及包含特定莫纳丁立体异构体、特定莫纳丁立体异构体混合物和/或通过体内（例如细胞内）或体外生物合成途径产生的莫纳丁的饮料组合物。