o-nitrobenzenesulfenyl-L-asparagine 2,4,5-trichlorophenyl ester | 42381-92-0

• 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
• 英文名称: o-nitrobenzenesulfenyl-L-asparagine 2,4,5-trichlorophenyl ester
• 英文别名: o-nitrobenzenesulphenylasparagine 2,4,5-trichlorophenyl ester
• CAS: 42381-92-0
• 化学式: C₁₆H₁₂Cl₃N₃O₅S
• 分子量: 464.713
• InChiKey: QAZVDBCLWIMIIC-NSHDSACASA-N

物化性质

• 沸点：
  693.6±65.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.0
• 重原子数：
  28.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  Tert-Butyloxycarbonyl-S-<2-(2-methyl-1-methoxycarbonylpropyl)>homocysteinyl-prolyl-leucyl-glycine Amide 、 o-nitrobenzenesulfenyl-L-asparagine 2,4,5-trichlorophenyl ester 在 N-乙基哌啶 作用下， 生成 o-Nitrobenzenesulphenylasparaginyl-S-(2-(2-methyl-1-methoxycarbonylpropyl))homocysteinyl-prolyl-leucyl-glycine Amide
  参考文献：
  名称：

  Synthesis and properties of carba-6-analogues of oxytocin containing a deaminopenicillamine residue in position 1

  摘要：

  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）。

  DOI：

  10.1135/cccc19842012

文献信息

• Synthesis of the amino-terminal decapeptide of human calcitonin, in which the disulfide bond is replaced by a thioether group
  作者：Zdenko Procházka、Karel Jošt

  DOI：10.1135/cccc19801305

  日期：——

  A fully protected amino-terminal decapeptide Ib with the sequence of human calcitonin, in which the S-S bridge was replaced by the S-CH₂ group (a so-called 7-carba-analogue), was synthetized mainly by the stepwise method. The cyclization of the linear decapeptide was performed by means of active ester.

  一种全保护的氨基末端十肽Ib，其序列与人降钙素相同，其中S-S桥被S-CH2基团（所谓的7-碳代物）所取代，主要通过逐步法合成。线性十肽的环化是通过活性酯实现的。
• 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。
• Synthesis of oxytocin analogues modified in the tripeptide side-chain by condensation of aminoterminal linear hexapeptide with the carboxyterminal tripeptide
  作者：Jan Hlaváček、Tomislav Barth、Karel Bláha、Karel Jošt

  DOI：10.1135/cccc19790275

  日期：——

  For the synthesis of oxytocin (Ia) analogues modified in the carboxyterminal part of the molecule, a method based on the condensation of protected aminoterminal hexapeptide with tripeptides by the action of dicyclohexylcarbodiimide and pentafluorophenol in the presence of 1-hydroxybenzotriazole was devised. Using this method [7-[U-¹³C]proline]oxytocin (Ib), des-9-glycine-oxytocin (Ic) and methyl ester of oxytocinoic acid ([9-glycine methyl ester]oxytocin) (Id) were prepared.

  对于氧催产素（Ia）分子的羧基端部分进行修饰的合成，设计了一种基于受保护的氨基端六肽与三肽通过二环己基碳二亚胺和五氟苯酚在1-羟基苯并三唑存在下的缩合反应的方法。使用这种方法制备了[7-[U-¹³C]脯氨酸]氧催产素（Ib）、去九甘氨酸氧催产素（Ic）和氧催产酸甲酯（[9-甘氨酸甲酯]氧催产素）（Id）。