(2S)-4-hydroxy-4-methylglutamic acid | 81276-00-8

• 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: (2S)-4-hydroxy-4-methylglutamic acid
• 英文别名: L-4-methyl-4-hydroxyglutamic acid；4-Hydroxy-4-methylglutamic acid；(4S)-4-amino-2-hydroxy-2-methylpentanedioic acid
• CAS: 81276-00-8
• 化学式: C₆H₁₁NO₅
• 分子量: 177.157
• InChiKey: ONTAOGAXMOTXQW-FWRGRRDFSA-N

物化性质

• 沸点：
  438.6±45.0 °C(Predicted)
• 密度：
  1.495±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.9
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  121
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  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

文献信息

• Methods for treating of skin conditions with retinoid double conjugate compounds
  申请人：US COSMECEUTECHS LLC

  公开号：US10123960B2

  公开（公告）日：2018-11-13

  A double conjugate molecule made of a retinoid, an organic acid, particularly an a-hydroxy acid, and an alcohol or acyl group, is provided which is useful in treating skin conditions, particularly aging. The retinoid, organic acid, and alcohol/acyl group are preferably linked via ester bonds.

  提供一种由视黄醇、有机酸（特别是α-羟基酸）和醇或酰基组成的双共轭分子，可用于治疗皮肤状况，特别是衰老。视黄醇、有机酸和醇/酰基组最好通过酯键连接。
• 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。
• Production of monatin and monatin precursors
  申请人：McFarlan C. Sara

  公开号：US20050221455A1

  公开（公告）日：2005-10-06

  Methods and compositions that can be used to make monatin or salt thereof 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 producing 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.

  本发明提供了可用于从葡萄糖、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-酮戊酸制备莫纳汀或其盐的方法和组合物。还揭示了制备吲哚-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。所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。
• Polypeptides and biosynthetic pathways for the production of stereoisomers of monatin and their precursors
  申请人：Brazeau J. Brian

  公开号：US20060252135A1

  公开（公告）日：2006-11-09

  Monatin and certain stereoisomers of monatin, such as R,R monatin and S,R monatin, as well as salts thereof, are produced using polypeptides and biosynthetic pathways. These polypeptides and biosynthetic pathways are also useful in the production of R-2-hydroxy-2-(indoly-3-ylmethyl)-4-keto glutaric acid, an intermediate that is formed in certain monatin synthesis pathways, including some biosynthetic pathways.

  Monatin和某些立体异构体，如R，R monatin和S，R monatin，以及它们的盐，是使用多肽和生物合成途径生产的。这些多肽和生物合成途径也可用于生产R-2-羟基-2-（吲哚-3-基甲基）-4-酮戊二酸，这是某些monatin合成途径中形成的中间体，包括一些生物合成途径。
• Aldolases, nucleic acids encoding them and methods for making and using them
  申请人：Burke Ellen

  公开号：US20080020435A1

  公开（公告）日：2008-01-24

  This invention relates to polypeptides having aldolase activity, including pyruvate activity such as, without limitation, HMG and/or KHG aldolase activity, polynucleotides encoding these polypeptides, and methods of making and using these polynucleotides and polypeptides. In some embodiments, the invention is directed to polypeptides having aldolase activity, including pyruvate activity such as, without limitation, HMG and/or KHG aldolase activity, including thermostable and thermotolerant activity, and polynucleotides encoding these enzymes, and making and using these polynucleotides and polypeptides. The polypeptides in accordance with the invention can be used in a variety of pharmaceutical, agricultural and industrial contexts. In some embodiments, the invention provides polypeptides and biosynthetic pathways that are useful in the production of R-2-hydroxy 2-(indol-3ylmethyl)-4-keto glutaric acid (R-MP) and certain stereoisomers of monatin, such as R,R and S,R monatin, and salts thereof, as well as certain stereoisomers of monatin derivatives, such as the R,R and S,R configurations, and salts thereof.

  本发明涉及具有醛缩酶活性的多肽，包括丙酮酸活性，例如，但不限于HMG和/或KHG醛缩酶活性，编码这些多肽的多核苷酸以及制备和使用这些多核苷酸和多肽的方法。在某些实施例中，本发明涉及具有醛缩酶活性的多肽，包括丙酮酸活性，例如，但不限于HMG和/或KHG醛缩酶活性，包括热稳定和热耐受活性，以及编码这些酶的多核苷酸，并制备和使用这些多核苷酸和多肽。根据本发明的多肽可以在各种制药、农业和工业背景下使用。在某些实施例中，本发明提供了用于生产R-2-羟基2-(吲哚-3-甲基)-4-酮戊二酸（R-MP）和某些单味噌味酸的立体异构体（如R，R和S，R单味噌味酸及其盐）以及某些单味噌味酸衍生物的立体异构体（如R，R和S，R构型及其盐）的多肽和生物合成途径。