α-N-oxalyl-L-α,β-diaminopropionic acid | 61277-72-3

• 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: α-N-oxalyl-L-α,β-diaminopropionic acid
• 英文别名: α-N-Oxalyl-diaminopropionsaeure；L-3-Amino-2-oxalylamino-propionsaeure；3-Amino-N-(carboxycarbonyl)-L-alanine；(2S)-3-amino-2-(oxaloamino)propanoic acid
• CAS: 61277-72-3
• 化学式: C₅H₈N₂O₅
• 分子量: 176.129
• InChiKey: FNXJKVNOUQAQMB-REOHCLBHSA-N

物化性质

• 密度：
  1.596±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -4.1
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  copper(II) acetate monohydrate 、 α-N-oxalyl-L-α,β-diaminopropionic acid 以 not given 为溶剂， 生成 α-N-oxalyl-L-α,β-diaminopropionic acid copper(II) complex
  参考文献：
  名称：

  Metal ion complexes of amino acids. Part II [1]. The copper complexes of the α- and β-isomers of N-oxalyl-L-α,β-diaminopropionic acid.

  摘要：

  DOI：

  10.1016/s0020-1693(00)85810-7
• 作为产物：
  描述：

  3-[(羧基羰基)氨基]-L-丙氨酸 以 重水 为溶剂， 生成 α-N-oxalyl-L-α,β-diaminopropionic acid
  参考文献：
  名称：

  二氨基酸的 N-草酰衍生物的热异构化

  摘要：

  摘要 豆科植物 Lathyrus sativus 的神经毒性成分 β-N-草酰-α,β-二氨基丙酸被热异构化为含有无毒 α-N-草酰-α,β-的平衡混合物 (60/40)。二氨基丙酸。通过从 α-异构体开始建立相同的平衡混合物，但需要更长的时间。α- 和 γ-N-草酰基-α,γ-二氨基丁酸也经历了热诱导异构化，草酰基的 α-γ 或 γ-α 迁移。δ-N-草酰鸟氨酸和 eN-草酰赖氨酸在这些条件下不会异构化。较高同系物不发生异构化的观察结果表明反应的分子内性质。

  DOI：

  10.1016/0031-9422(93)85034-o

文献信息

• Synthesis of α- and β-N-oxalyl-l-α,β-diaminopropionic acids and their isolation from seeds of Lathyrus sativus
  作者：Frances Lynne Harrison、P.B. Nunn、R.R. Hill

  DOI：10.1016/s0031-9422(00)94362-0

  日期：1977.1

  Abstract The α- and β- N -oxalyl derivatives of l -α,β-diaminopropionic acid have been chemically synthesized and also isolated from seed extracts of Lathyrus sativus . Chemical and physical properties of the natural and synthetic isomers were in good agreement. The toxicity of the α-isomer to chicks was evaluated and compared with that of the β-isomer.

  摘要 L-α,β-二氨基丙酸的α-和β-N-草酰衍生物已经化学合成，也从Lathyrus sativus的种子提取物中分离出来。天然和合成异构体的化学和物理性质非常一致。评估了α-异构体对小鸡的毒性并与β-异构​​体的毒性进行了比较。
• Kinetics studies on thermal isomerization of β-N-oxalyl-L-α,β-diaminopropionic acid by capillary zone electrophoresis
  作者：Liang Zhao、Xhixiao Li、Guanbin Li、Xingguo Chen、Zhide Hu

  DOI：10.1039/a902229e

  日期：——

  The reciprocal thermal isomerization in aqueous solution between neurotoxic nonprotein amino acid β-N-oxalyl-L-α,β-diaminopropionic acid (β-ODAP) in seeds of Lathyrussativus (LS; grass pea) and its nontoxic isomer α-N-oxalyl-L-α,β-diaminopropionic acid (α-ODAP) was studied using capillary zone electrophoresis (CZE) in the range from pH=2.5 to pH=13 at T=75°C, and a decrease of the equilibrium concentration ratio of α-ODAP with the increase of pH of the solution was found. In the range of temperatures 55–95°C, The rate constants have been measured and thermodynamic parameters such as activation energy (Ea) and the pre-exponential factor (A) have been calculated.

  利用毛细管区带电泳技术（CZE），在pH值范围2.5至13、温度75°C的条件下，研究了草豌豆（Lathyrus sativus，简称LS）种子中神经毒性非蛋白质氨基酸β-N-草酰基-L-α,β-二氨基丙酸（β-ODAP）与其无毒异构体α-N-草酰基-L-α,β-二氨基丙酸（α-ODAP）在水溶液中的相互热异构化反应。研究发现，随着溶液pH值的增加，α-ODAP的平衡浓度比率下降。在温度55至95°C的范围内，测定了速率常数，并计算了活化能（Ea）和指数前因子（A）等热力学参数。
• l-2-Oxalylamino-3-aminopropionic acid, an isomer of Lathyrus sativus neurotoxin
  作者：Grace Wu、Stephen B. Bowlus、Sook Kim Kyung、Betty E. Haskell

  DOI：10.1016/0031-9422(76)85088-1

  日期：1976.1

  The first chemical synthesis of l -2-oxalylamino-3-aminopropionic acid, an isomer of the Lathyrus sativus neurotoxin, is described. Studies on its biological properties are reported. Experiments with l -3-[14C-oxalyl]amino-2- aminopropionic acid show that the amount of 2-oxalylamino isomer detectable in seed extracts can be accounted for by rearrangement which occurs during isolation.

  摘要 描述了 Lathyrus sativus 神经毒素的异构体 l -2-oxalylamino-3-aminopropionic 酸的首次化学合成。报道了对其生物学特性的研究。用1-3-[14C-草酰]氨基-2-氨基丙酸的实验表明，种子提取物中可检测到的2-草酰氨基异构体的量可以通过分离过程中发生的重排来解释。
• Thermal isomerization of the neurotoxin β-N-oxalyl-l-α,β-diaminopropionic acid
  作者：Abebaw Belay、Ghirma Moges、Theodros Solomon、Gillis Johansson

  DOI：10.1016/s0031-9422(96)00826-6

  日期：1997.5

  The rate constants and reaction order for the conversion of the neurotoxin beta-ODAP to alpha-ODAP have been determined, after off-line thermal treatment, using the recently developed flow injection system for the neurotoxin based on a glutamate oxidase reactor. The effects of the initial concentration of the toxin, temperature and pH on the kinetics and the equilibrium of the endothermic process were examined. The conversion followed a zero order rate law. The reaction rate at pH 7 increased by about two-fold for every 10 degrees temperature rise. The rate at pH 2 was about 60% higher than at pH 7. (C) 1997 Elsevier Science Ltd.
• Thermal isomerization of N-oxalyl derivatives of diamino acids
  作者：Berhanu M. Abegaz、Peter B. Nunn、André De Bruyn、Fernand Lambein

  DOI：10.1016/0031-9422(93)85034-o

  日期：1993.7

  sativus, β-N-oxalyl-α,β-diaminopropionic acid, was thermally isomerized to an equilibrium mixture (60/40) containing the non-toxic α-N-oxalyl-α,β-diaminopropionic acid. The same equilibrium mixture was established by starting with the α-isomer but required longer time. α- and γ-N-Oxalyl-α,γ-diaminobutyric acids also underwent thermally induced isomerization with α-γ, or γ-α migration of the oxalyl group

  摘要 豆科植物 Lathyrus sativus 的神经毒性成分 β-N-草酰-α,β-二氨基丙酸被热异构化为含有无毒 α-N-草酰-α,β-的平衡混合物 (60/40)。二氨基丙酸。通过从 α-异构体开始建立相同的平衡混合物，但需要更长的时间。α- 和 γ-N-草酰基-α,γ-二氨基丁酸也经历了热诱导异构化，草酰基的 α-γ 或 γ-α 迁移。δ-N-草酰鸟氨酸和 eN-草酰赖氨酸在这些条件下不会异构化。较高同系物不发生异构化的观察结果表明反应的分子内性质。