pGlu-Leu-Gly-NH2 | 39705-61-8

• 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: pGlu-Leu-Gly-NH2
• 英文别名: L-pyroglutamyl-L-leucylglycinamide；5-Oxo-L-prolyl-L-leucylglycinamide；(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-4-methyl-1-oxopentan-2-yl]-5-oxopyrrolidine-2-carboxamide
• CAS: 39705-61-8
• 化学式: C₁₃H₂₂N₄O₄
• 分子量: 298.342
• InChiKey: WIDQRRFLNXDVGE-IUCAKERBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  21
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  130
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  CBZ-L-焦谷氨酸 在 palladium on activated charcoal N-甲基吗啉 、 盐酸 、 氢气 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 甲醇 为溶剂， 反应 1.17h， 生成 pGlu-Leu-Gly-NH2
  参考文献：
  名称：

  Synthesis of Pro-Leu-Gly-NH2 analogs modified at the prolyl residue and evaluation of their effects on the receptor binding activity of the central dopamine receptor agonist, ADTN

  摘要：

  Several analogues of L-prolyl-L-leucylglycinamide (PLG) were synthesized wherein the prolyl residue was replaced with other heterocyclic amino acid residues. Among the analogues synthesized were D-Pro-Leu-Gly-NH2 (2), less than Glu-Leu-Gly-NH2 (3), Thz-Leu-Gly-NH2 (4), Pip-Leu-Gly-NH2 (5), Aze-Leu-Gly-NH2 (6), L-delta 3,4-Pro-Leu-Gly-NH2 (7), and D-delta 3,4-Pro-Leu-Gly-NH2 (8). These analogues were tested for their ability to enhance the binding of the agonist 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene to central dopamine receptors. Analogues 2, 3, and 5-7 showed activity comparable to that of PLG, while the tripeptides 4 and 8 were found to be inactive. The results show that the N-terminal prolyl residue of PLG is not an essential requirement for this tripeptide's ability to modulate dopamine receptors.

  DOI：

  10.1021/jm00160a052

文献信息

• Synthesis of thyrotropin-releasing hormone analogs. 2. Tripeptides structurally greatly different from TRH with high central nervous system activity
  作者：Tamas Szirtes、Lajos Kisfaludy、Eva Palosi、Laszlo Szporny

  DOI：10.1021/jm00159a015

  日期：1986.9

  from TRH. In spite of this fact, 7 of the 17 analogues (1, 2, 8-10, 16, and 17) have stronger anticataleptic effect than TRH, with negligible or no hormonal potency. The highest CNS activity was achieved when pyroglutamic acid was replaced by pyro-2-aminoadipic acid at the N-terminus [pAad-Leu-Pro-NH2, 1 (RGH 2202), and pAad-Nva-Pro-NH2,2]. A novel synthesis of L-2-aminoadipic acid suitable for large-scale

  通过五氟苯基酯法合成了一系列新的促甲状腺激素释放激素（TRH）类似物，这些类似物是通过进一步修饰我们最有效的中枢神经系统（CNS）在两个末端刺激中性三肽而获得的，并测试了CNS和促甲状腺激素（TSH）释放活动。[Leu2]中的吡咯-2-氨基己二酸，2-氧代咪唑烷-4-羧酸或γ-丁内酯-γ-羧酸取代脯氨酸谷氨酸，脯氨酸由哌啶酸，噻唑烷-4-羧酸或高脯氨酸代替脯氨酸。 -和[Nva2] TRH导致三肽结构上与TRH大不相同。尽管如此，17种类似物中的7种（1、2、8-10、16和17）比TRH具有更强的抗感性作用，激素作用微乎其微或无。当焦谷氨酸在N端被焦-2-氨基己二酸取代时，CNS活性最高[pAad-Leu-Pro-NH2，1（RGH 2202）和pAad-Nva-Pro-NH2,2]。还描述了适用于大规模制备的L-2-氨基己二酸的新颖合成。
• Synthesis of Pro-Leu-Gly-NH2 analogs modified at the prolyl residue and evaluation of their effects on the receptor binding activity of the central dopamine receptor agonist, ADTN
  作者：Rodney L. Johnson、G. Rajakumar、Kuo Long Yu、Ram K. Mishra

  DOI：10.1021/jm00160a052

  日期：1986.10

  Several analogues of L-prolyl-L-leucylglycinamide (PLG) were synthesized wherein the prolyl residue was replaced with other heterocyclic amino acid residues. Among the analogues synthesized were D-Pro-Leu-Gly-NH2 (2), less than Glu-Leu-Gly-NH2 (3), Thz-Leu-Gly-NH2 (4), Pip-Leu-Gly-NH2 (5), Aze-Leu-Gly-NH2 (6), L-delta 3,4-Pro-Leu-Gly-NH2 (7), and D-delta 3,4-Pro-Leu-Gly-NH2 (8). These analogues were tested for their ability to enhance the binding of the agonist 2-amino-6,7-dihydroxy-1,2,3,4-tetrahydronaphthalene to central dopamine receptors. Analogues 2, 3, and 5-7 showed activity comparable to that of PLG, while the tripeptides 4 and 8 were found to be inactive. The results show that the N-terminal prolyl residue of PLG is not an essential requirement for this tripeptide's ability to modulate dopamine receptors.