(R)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxo-pentanedioic acid | 735328-71-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (R)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxo-pentanedioic acid
• 英文别名: (2R)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxopentanedioic acid
• CAS: 735328-71-9
• 化学式: C₁₄H₁₃NO₆
• 分子量: 291.26
• InChiKey: SLWQCDYJBNGHQV-CQSZACIVSA-N

物化性质

• 沸点：
  609.1±55.0 °C(Predicted)
• 密度：
  1.577±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  128
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  D-丙氨酸 、 sodium pyruvate 在 D-amino-acid transaminase potassium phosphate 、 磷酸吡哆醛 、 4-羟乙基哌嗪丙磺酸 、 magnesium chloride 作用下， 以 水 为溶剂， 生成 (2R,4R)-monatin 、 (R)-2-hydroxy-2-(1H-indol-3-ylmethyl)-4-oxo-pentanedioic acid
  参考文献：
  名称：

  Methods And Systems For Increasing Production of Equilibrium Reactions

  摘要：

  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。

  公开号：

  US20080015361A1

文献信息

• Variant aldolase and processes for producing an optically active IHOG and an optically active monatin using the same
  申请人：Sugiyama Masakazu

  公开号：US20050244939A1

  公开（公告）日：2005-11-03

  The present invention relates to variant aldolase enzymes that are modified so as to produce IHOG, a process for producing an optically active IHOG using the same, and a process for producing an optically active monatin.

  本发明涉及变种醛缩酶酶，经过改良以产生IHOG，使用相同的方法生产光学活性IHOG的过程，以及生产光学活性莫纳丁的过程。
• Novel aldolase, and method for producing optically active IHOG and monatin
  申请人：Sugiyama Masakazu

  公开号：US20060003426A1

  公开（公告）日：2006-01-05

  The present invention relates to a method for producing optically active IHOG, which can in turn be used for the production of monatin. The present invention further relates to a method for producing optically active monatin, and aldolase used for these methods. As such, the present invention enables the synthesis of 4-(Indole-3-ylmethyl)-4-hydroxy-2-oxoglutaric acid with high optical purity, which is useful as an intermediate in the synthesis of optically active monatin, from indole pyruvic acid and pyruvic acid (or oxaloacetic acid).

  本发明涉及一种制备光学活性IHOG的方法，该方法可用于生产莫纳丁。本发明还涉及一种制备光学活性莫纳丁的方法，以及用于这些方法的醛酸酯酶。因此，本发明使得从吲哚丙酮酸和丙酮酸（或草酰乙酸）制备出具有高光学纯度的4-（吲哚-3-基甲基）-4-羟基-2-酮戊二酸成为可能，该化合物在光学活性莫纳丁的合成中作为中间体具有重要用途。
• 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。
• NOVEL ALDOLASE, AND METHOD FOR PRODUCING OPTICALLY ACTIVE IHOG AND MONATIN
  申请人：SUGIYAMA Masakazu

  公开号：US20090258403A1

  公开（公告）日：2009-10-15

  The present invention relates to a method for producing optically active IHOG, which can in turn be used for the production of monatin. The present invention further relates to a method for producing optically active monatin, and aldolase used for these methods. As such, the present invention enables the synthesis of 4-(Indole-3-ylmethyl)-4-hydroxy-2-oxoglutaric acid with high optical purity, which is useful as an intermediate in the synthesis of optically active monatin, from indole pyruvic acid and pyruvic acid (or oxaloacetic acid).

  本发明涉及一种生产光学活性IHOG的方法，该方法可用于生产莫纳丁。本发明还涉及一种生产光学活性莫纳丁的方法和用于这些方法的醛缩酶。因此，本发明能够使4-（吲哚-3-甲基）-4-羟基-2-酮戊酸以高光学纯度合成，该化合物在从吲哚丙酮酸和丙酮酸（或草酰乙酸）合成光学活性莫纳丁的中间体中非常有用。
• 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。