3,4-二氢-2H-吡咯-2-羧酸 | 2906-39-0

• 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
• 中文名称: 3,4-二氢-2H-吡咯-2-羧酸
• 英文名称: Δ¹-pyrroline-5-carboxylate
• 英文别名: DL-1-pyrroline-5-carboxylic acid；1-pyrroline-5-carboxylate；DL-P5C；3,4-dihydro-2H-pyrrole-2-carboxylic acid；3,4-Dihydro-2H-pyrrol-2-carbonsaeure；Δ1-Pyrrolin-carbonsaeure-(5)；3,4-dihydro-2H-pyrrole-2-carboxylic acid
• CAS: 2906-39-0
• 化学式: C₅H₇NO₂
• mdl: MFCD17013422
• 分子量: 113.116
• InChiKey: DWAKNKKXGALPNW-UHFFFAOYSA-N

物化性质

• 熔点：
  140-142 °C (decomp)(Solv: water (7732-18-5))
• 沸点：
  304.1±42.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)
• 物理描述：
  Solid

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  8
• 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：
  49.7
• 氢给体数：
  1
• 氢受体数：
  3

ADMET

毒理性

• 致癌物分类

对人类不具有致癌性（未被国际癌症研究机构IARC列名）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

长期高水平的吡咯啉-5-羧酸与至少5种遗传代谢病有关，包括：高脯氨酸血症I型、高脯氨酸血症II型、亚氨基甘氨酸尿症、脯氨酸血症II型和丙酮酸羧化酶缺乏症。

Chronically high levels of pyrroline-5-carboxylate are associated with at least 5 inborn errors of metabolism including: Hyperprolinemia Type I, Hyperprolinemia Type II, Iminoglycinuria, Prolinemia Type II and Pyruvate carboxylase deficiency.

来源:Toxin and Toxin Target Database (T3DB)

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3,4-二氢-2H-吡咯-2-羧酸 在 (4S-2H)-NADH 、 NosF gene from Escherichia colie 、 三羟甲基氨基甲烷 作用下， 以 水 为溶剂， 生成 (2S,4R)-<4-2H1>-proline
  参考文献：
  名称：

  Biosynthesis of 4-Methylproline in Cyanobacteria:  Cloning of nosE and nosF Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities

  摘要：

  The biosynthesis of the unusual amino acid 4-methylproline in the Nostoc genus of cyanobacteria was investigated on the genetic and enzymatic level. Two genes involved in the biosynthesis were cloned and the corresponding enzymes, a zinc-dependent long-chain dehydrogenase and a Delta(1)-pyrroline-5-carboxylic acid (P5C) reductase homologue, were overexpressed in Escherichia coli and biochemically characterized. Putative substrates were synthesized to test enzyme substrate specificities, and deuterium labeling studies were carried out to reveal the stereospecificities of the enzymatic reactions with respect to the substrates as well as to the coenzymes.

  DOI：

  10.1021/jo026479q
• 作为产物：
  描述：

  4-acetamido-4,4-bis(ethyloxycarbonyl)butyraldehyde 在 盐酸 作用下， 生成 3,4-二氢-2H-吡咯-2-羧酸
  参考文献：
  名称：

  Glutamic γ-Semialdehyde and Δ¹-Pyrroline-5-carboxylic Acid, Intermediates in the Biosynthesis of Proline^1,2

  摘要：

  DOI：

  10.1021/ja01121a025

文献信息

• Crystal Structures and Kinetics of Monofunctional Proline Dehydrogenase Provide Insight into Substrate Recognition and Conformational Changes Associated with Flavin Reduction and Product Release
  作者：Min Luo、Benjamin W. Arentson、Dhiraj Srivastava、Donald F. Becker、John J. Tanner

  DOI：10.1021/bi301312f

  日期：2012.12.18

  and the β1−α1 loop. The FAD ribityl chain adopts two conformations in the E–S complex, which is unprecedented for flavoenzymes. One of the conformations is novel for the PRODH superfamily and may contribute to the low substrate affinity of Deinococcus PRODH. Reduction of the crystalline enzyme–inhibitor complex causes profound structural changes, including 20° butterfly bending of the isoalloxazine

  脯氨酸脱氢酶 (PRODH) 催化脯氨酸的 FAD 依赖性氧化为 Δ 1 -pyrroline-5-carboxylate，这是脯氨酸分解代谢的第一步。在这里，我们报告了来自耐辐射奇异球菌的脯氨酸脱氢酶的结构，氧化态与脯氨酸类似物l-四氢呋喃复合，以及脯氨酸位点空置的还原态。该类似物与FAD 异咯嗪的si面结合，并通过螺旋 α8 和 β1-α1 环保护免受大量溶剂的影响。FAD 核糖基链在 E-S 复合物中采用两种构象，这对于黄素酶来说是前所未有的。其中一种构象是 PRODH 超家族的新构象，可能导致其底物亲和力低奇异球菌专业版。结晶酶-抑制剂复合物的减少会导致深刻的结构变化，包括异恶嗪的 20°蝶形弯曲、ribityl 的曲轴旋转、α8 移动 1.7 Å、β1-α1 环的重新配置以及 Arg291-Glu64 的破裂离子对。这些变化极大地打开了活性位点，促进了产品的释放，并使电子受体能够接触到减少的黄素。这些结构表明，在
• Synthesis and Evaluation of Effective Inhibitors of Plant δ¹-Pyrroline-5-carboxylate Reductase
  作者：Giuseppe Forlani、Łukasz Berlicki、Mattia Duò、Gabriela Dziędzioła、Samuele Giberti、Michele Bertazzini、Paweł Kafarski

  DOI：10.1021/jf401234s

  日期：2013.7.17

  Analogues of previously studied phenyl-substituted aminomethylene-bisphosphonic acids were synthesized and evaluated as inhibitors of Arabidopsis thaliana delta(1)-pyrroline-5-carboxylate reductase. With the aim of improving their effectiveness, two main modifications were introduced into the inhibitory scaffold: the aminomethylenebisphosphonic moiety was replaced with a hydroxymethylenebisphosphonic group, and the length of the molecule was increased by replacing the methylene linker with an ethylidene chain. In addition, chlorine atoms in the phenyl ring were replaced with various other substituents. Most of the studied derivatives showed activity in the rnicromolar to millimolar range, with two of them being more effective than the lead compound, with concentrations inhibiting 50% of enzyme activity as low as 50 mu M. Experimental evidence supporting the ability of these inhibitors to interfere with proline synthesis in vivo is also shown.
• Osugi, Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan, 1958, vol. 78, p. 1318,1322
  作者：Osugi

  DOI：——

  日期：——
• MIXSON, A. JAMES;GRANGER, ALNORA N.;PHANG, JAMES M., ANAL. LETT., 24,(1991) N, C. 625-641
  作者：MIXSON, A. JAMES、GRANGER, ALNORA N.、PHANG, JAMES M.

  DOI：——

  日期：——
• Biosynthesis of 4-Methylproline in Cyanobacteria:  Cloning of <i>n</i><i>osE</i> and <i>n</i><i>osF</i> Genes and Biochemical Characterization of the Encoded Dehydrogenase and Reductase Activities
  作者：Hendrik Luesch、Dietmar Hoffmann、Joan M. Hevel、Julia E. Becker、Trimurtulu Golakoti、Richard E. Moore

  DOI：10.1021/jo026479q

  日期：2003.1.1

  The biosynthesis of the unusual amino acid 4-methylproline in the Nostoc genus of cyanobacteria was investigated on the genetic and enzymatic level. Two genes involved in the biosynthesis were cloned and the corresponding enzymes, a zinc-dependent long-chain dehydrogenase and a Delta(1)-pyrroline-5-carboxylic acid (P5C) reductase homologue, were overexpressed in Escherichia coli and biochemically characterized. Putative substrates were synthesized to test enzyme substrate specificities, and deuterium labeling studies were carried out to reveal the stereospecificities of the enzymatic reactions with respect to the substrates as well as to the coenzymes.