(S)-5-氨基-2-羟基-5-氧代戊酸 | 53363-45-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (S)-5-氨基-2-羟基-5-氧代戊酸
• 英文名称: L-2-hydroxyglutaramic acid
• 英文别名: L-2-HGM；2-Hydroxyglutarsaeure-5-amid；(2S)-5-Amino-2-hydroxy-5-oxopentanoic acid
• CAS: 53363-45-4
• 化学式: C₅H₉NO₄
• 分子量: 147.131
• InChiKey: YEQXTNAAHMATGV-VKHMYHEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-5-氨基-2-羟基-5-氧代戊酸 在 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 、 sodium hydroxide 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.25h， 生成 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
• 作为产物：
  描述：

  L-谷氨酰胺 生成 (S)-5-氨基-2-羟基-5-氧代戊酸
  参考文献：
  名称：

  642.谷氨酸，谷氨酰胺和γ-氨基戊酸脱氨基后内酯化的空间过程

  摘要：

  DOI：

  10.1039/jr9610003278

文献信息

• 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.
• 642. The steric course of lactonisation following the deamination of glutamic acid, glutamine, and γ-aminovaleric acid
  作者：A. T. Austin、J. Howard

  DOI：10.1039/jr9610003278

  日期：——