2-hydroxy-5-oxopyrrolidine-2-carboxylic acid | 52100-66-0

• 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: 2-hydroxy-5-oxopyrrolidine-2-carboxylic acid
• 英文别名: 2-hydroxy-5-oxoproline；5-Hydroxypyroglutamat；α-Ketoglutaram-saeure；2-Pyrrolidon-5-hydroxy-5-carbonsaeure；2-Hydroxy-5-oxo-prolin
• CAS: 52100-66-0
• 化学式: C₅H₇NO₄
• 分子量: 145.115
• InChiKey: XWXRVFUXLXYGHK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-(trifluoromethyl)benzyl 2-hydroxy-5-oxopyrrolidine-2-carboxylate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 0.08h， 以93.6%的产率得到2-hydroxy-5-oxopyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of α-Ketoglutaramic acid

  摘要：

  alpha-Ketoglutaramic acid (KGM, alpha-ketoglutaramate), also known as 2-oxoglutaramic acid (OGM, 2-oxoglutaramate), is a substrate of omega-amidase, also known as Nitrilase 2 (NIT2), and is essential for studying the canonical role of omega-amidase, as well as its role in multiple diseases. Until now, KGM used for biological studies has been prepared most often by the enzymatic oxidation of L-glutamine using snake venom L-amino acid oxidase, which provides KGM as an aqueous solution, containing by-products including 5-oxoproline and alpha-ketoglutarate. The enzymatic method for KGM preparation, therefore, cannot provide pure product or an accurate percent yield evaluation. Here, we report a synthetic method for the preparation of this important substrate, KGM, in 3 steps, from L-2-hydroxyglutaramic acid, in pure form, in 53% overall yield.

  DOI：

  10.1016/j.ab.2020.113862

文献信息

• Preparation of 2-hydroxy-5-oxoproline and analogs thereof
  申请人：The Regents of the University of California

  公开号：US06288240B1

  公开（公告）日：2001-09-11

  The compound 2-hydroxy-5-oxoproline and analogs thereof may be used to produce an increase in carbon dioxide fixation, growth, dry weight, nutritional value (proteins and amino acids), nodulation and nitrogen fixation and photosynthetically derived chemical energy when applied to plants through their roots and/or through their foliar portions. The present invention includes an essentially quantitative chemical synthesis for this compound which is performed in a single step reaction of Fremy's Salt (potassium nitrosodisulphonate) with either glutamine or 2-pyrrolidone-5-carboxylic acid. Fremy's salt (potassium nitrosodisulphonate) is available commercially, or can be readily synthesized.

  化合物2-羟基-5-氧代脯氨酸及其类似物可用于通过植物的根和/或叶面部位施用，以产生增加二氧化碳固定、生长、干重、营养价值（蛋白质和氨基酸）、结瘤和氮固定以及光合产生的化学能量。本发明包括一种基本定量的化学合成方法，该方法在一步反应中使用弗雷米盐（亚硝基二磺酸钾）和谷氨酰胺或2-吡咯烷酮-5-羧酸。弗雷米盐（亚硝基二磺酸钾）可以在商业上获得，或者可以很容易地合成。
• Otani; Meister, Journal of Biological Chemistry, 1957, vol. 224, p. 137,143
  作者：Otani、Meister

  DOI：——

  日期：——
• Meister, Journal of Biological Chemistry, 1953, vol. 200, p. 571,572, 574
  作者：Meister

  DOI：——

  日期：——
• Thayer; Horowitz, Journal of Biological Chemistry, 1951, vol. 192, p. 755,761
  作者：Thayer、Horowitz

  DOI：——

  日期：——
• Synthesis of α-Ketoglutaramic acid
  作者：Dunxin Shen、Laken Kruger、Tyler Deatherage、Travis T. Denton

  DOI：10.1016/j.ab.2020.113862

  日期：2020.10

  alpha-Ketoglutaramic acid (KGM, alpha-ketoglutaramate), also known as 2-oxoglutaramic acid (OGM, 2-oxoglutaramate), is a substrate of omega-amidase, also known as Nitrilase 2 (NIT2), and is essential for studying the canonical role of omega-amidase, as well as its role in multiple diseases. Until now, KGM used for biological studies has been prepared most often by the enzymatic oxidation of L-glutamine using snake venom L-amino acid oxidase, which provides KGM as an aqueous solution, containing by-products including 5-oxoproline and alpha-ketoglutarate. The enzymatic method for KGM preparation, therefore, cannot provide pure product or an accurate percent yield evaluation. Here, we report a synthetic method for the preparation of this important substrate, KGM, in 3 steps, from L-2-hydroxyglutaramic acid, in pure form, in 53% overall yield.