2,4,5-Trichlorophenyl ester of o-nitrobenzenesulphenylglutamine | 42381-93-1

• 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: 2,4,5-Trichlorophenyl ester of o-nitrobenzenesulphenylglutamine
• 英文别名: o-nitrobenzenesulphenylglutamine 2,4,5-trichlorophenyl ester；o-nitrobenzenesulfenyl-L-glutamine 2,4,5-trichlorophenyl ester
• CAS: 42381-93-1
• 化学式: C₁₇H₁₄Cl₃N₃O₅S
• 分子量: 478.74
• InChiKey: LINSVOJRFHEPHM-LBPRGKRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.39
• 重原子数：
  29.0
• 可旋转键数：
  9.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  124.56
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2,4,5-Trichlorophenyl ester of o-nitrobenzenesulphenylglutamine 在 N-乙基哌啶 、 盐酸 、 C₄H₉ONO,HCl 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 生成 Methyl ester of S-benzyl-β-mercaptopropionyl-tyrosyl-isoleucyl-glutaminyl-asparaginyl-S-benzylcysteine
  参考文献：
  名称：

  Analogues of neurohypophysial hormones, containing tert-leucine: Synthesis and properties

  摘要：

  含有第8位tert-亮氨酸的催产素类似物，去氨基催产素和去氨基加压素，通过溶液中的片段缩合制备。在溶液中逐步合成得到第2位含有tert-亮氨酸的1-卡巴-和6-卡巴-去氨基催产素的类似物。[8-Tert-亮氨酸] 催产素被证明是这一系列中最有趣的物质；它表现出相对较高和特定的泌乳作用，并且与胰蛋白酶的裂解速度比催产素慢一个数量级。

  DOI：

  10.1135/cccc19820689

文献信息

• Synthesis and properties of carba-6-analogues of oxytocin containing a deaminopenicillamine residue in position 1
  作者：Michal Lebl、Tomislav Barth、Linda Servítová、Jiřina Slaninová、Pavel Hrbas

  DOI：10.1135/cccc19842012

  日期：——

  A study was made of the influence of the so-called carba substitution of the disulphide bridge on the properties of inhibitors obtained by the introduction of deaminopenicillamine into position 1 of the oxytocin molecule. Two analogues - [dPen¹]carba-6-oxytocin (Ia) and [dPen¹, Tyr(Me)²]carba-6-oxytocin (Ib) were prepared and their biological activities were assayed. Compound Ia is a strong agonist in the uterotonic assay in vivo (280 I.U./mg) and a weak antagonistin the pressor assay. Compound Ib inhibited the utertonic activity of oxytocin in vitro (pA₂ = 8.43) and in vivo (pA₂ = 7.13) as well as the pressor action of lysine vasopressin (pA₂ = 7.43).

  一项研究探讨了所谓的卡巴取代二硫键对通过在催产素分子的位置1引入去氨基青霉胺而获得的抑制剂性质的影响。制备了两个类似物-[dPen¹]carba-6-催产素（Ia）和[dPen¹, Tyr(Me)²]carba-6-催产素（Ib），并对它们的生物活性进行了测定。化合物Ia在子宫收缩试验中是强激动剂（280 I.U./mg），在压力试验中是弱拮抗剂。化合物Ib抑制了催产素的子宫活性（体外pA₂ = 8.43，体内pA₂ = 7.13）以及赖氨酸加压素的升压作用（pA₂ = 7.43）。
• Synthesis of oxytocin, arginine-vasopressin and its deamino-analogue using 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur
  作者：František Brtník、Milan Krojidlo、Tomislav Barth、Karel Jošt

  DOI：10.1135/cccc19810286

  日期：——

  Preparation of oxytocin, arginine-vasopressin and its deamino-analogue serves as an example of use of 2,4,6-trimethylbenzyl group for protection of the cysteine sulfur atom in the peptide synthesis. This modified benzyl group is sufficiently stable under conditions of solvolytic removal of common amino-protecting groups and it can be cleaved off under mild conditions with liquid hydrogen fluoride or trifluoromethanesulfonic acid.

  催产素、精氨酸加压素及其去氨基类似物的制备是使用2,4,6-三甲基苄基团保护肽合成中的半胱氨酸硫原子的一个例子。这种改性的苄基团在常见氨基保护基的溶解条件下足够稳定，并且可以在液态氢氟酸或三氟甲磺酸的温和条件下被去除。
• [7-Glycine]deamino-1-carba-vasopressin: Synthesis and pharmacological properties
  作者：František Brtník、Tomislav Barth、Karel Jošt

  DOI：10.1135/cccc19810278

  日期：——

  [8-Arginine]deamino-1-carba-vasopressin and its 7-glycine derivative were prepared by condensation of the amino-terminal, cyclic part of the molecule with carboxy-terminal tripeptide amides. Replacement of proline by glycine in the position 7 results in a substantial decrease in the vasopressin-like activities, the oxytocin-like activities remaining unchanged.

  [8-精氨酸]去氨基-1-卡巴压素及其7-甘氨酸衍生物是通过将分子的氨基末端环状部分与羧基末端三肽酰胺进行缩合反应制备的。在第7位上将脯氨酸替换为甘氨酸会导致血管加压素样活性显著降低，而催产素样活性保持不变。