o-nitrobenzenesulfenyl-L-isoleucine N-hydroxysuccinimide ester | 22215-87-8

• 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: o-nitrobenzenesulfenyl-L-isoleucine N-hydroxysuccinimide ester
• 英文别名: o-nitrobenzenesulphenylisoleucine N-hydroxysuccinimide ester
• CAS: 22215-87-8
• 化学式: C₁₆H₁₉N₃O₆S
• 分子量: 381.409
• InChiKey: JKIJQGFFOUWNTC-BONVTDFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  26.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  118.85
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  o-nitrobenzenesulfenyl-L-isoleucine N-hydroxysuccinimide ester 在 N-乙基哌啶 、 盐酸 、 sodium hydroxide 作用下， 以 甲醇 、 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 73.0h， 生成 lactam of tyrosyl-isoleucyl-leucyl-asparaginyl-S-(γ-carboxypropyl)cysteinyl-prolyl-leucyl-glycinamide
  参考文献：
  名称：

  Analogues of deamino-1-carba-oxytocin with an aliphatic amino acid in position 4: chemical synthesis and biological activities

  摘要：

  线性八肽通过溶液中的逐步合成制备。通过活性酯的方法进行环化，得到了缺氨基-1-卡巴-催产素的类似物，其中第4位的谷氨酰胺残基被异亮氨酸、亮氨酸或缬氨酸替代。测定了这些类似物的基本药理活性；它们的利尿作用低于催产素。

  DOI：

  10.1135/cccc19802714

文献信息

• Synthesis and chiroptical properties of heterodetic cyclic hexapeptides related to oxytocin ring moiety
  作者：Ivo Frič、Lyudmila I. Leonteva、Petr Maloň、Karel Jošt、Karel Bláha

  DOI：10.1135/cccc19801109

  日期：——

  Cyclic disulfides of cysteinyl-tetraglycyl-cysteine (Ia), cysteinyl-tyrosyl-triglycyl-cysteine (Ib) and cysteinyl-tyrosyl-isoleucyl-diglycyl-cysteine (Ic) were synthesized by classical methods of peptide synthesis. The actions of solvent and of side chains in the positions 2 and 3 on the conformational arrangement of the peptide backbone and the disulfide group were investigated by means of CD spectroscopy. Some mechanisms which co-operate in stabilizing the oxytocin conformation were identified. Hence, it may be deduced, that the amino acid sequence in the positions 1-3 determines the spatial arrangement characteristic for oxytocin, at least in a protonating medium.

  半胱氨酸-四甘氨酰-半胱氨酸（Ia）、半胱氨酸-酪氨酰-三甘氨酰-半胱氨酸（Ib）和半胱氨酸-酪氨酰-异亮氨酰-二甘氨酰-半胱氨酸（Ic）的环二硫化物是通过肽合成的经典方法合成的。通过圆二色谱法研究了溶剂和位置2和3的侧链对肽骨架和二硫键构象排列的影响。确定了一些在稳定催产素构象方面起作用的机制。因此，可以推断，在质子化介质中，位置1-3的氨基酸序列决定了催产素特征空间排列。
• 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。
• Synthesis and pharmacological properties of oxytocin analogues modified simultaneously in position 2 and in the disulfide bridge
  作者：Michal Lebl、Tomislav Barth、Karel Jošt

  DOI：10.1135/cccc19802855

  日期：——

  Analogues of deamino-6-carba-oxytocin, containing isoleucine, O-methyltyrosine or methionine in position 2, either in the sulfide or sulfoxide form, were prepared and studied pharmacologically. These compounds had considerably lower biological activities than the analogous compounds of the 1-carba series. Furthermore, analogues of [1,6-homolanthionine]deamino-oxytocin were prepared with O-methyltyrosine or isoleucine in position 2; these compounds had a certain degree of oxytocic activity.

  含有异亮氨酸、O-甲基酪氨酸或蛋氨酸的去氨基-6-卡巴-催产素类似物，位于2号位置，可以是硫醚或亚硫酸盐形式。这些化合物的生物活性比1-卡巴系列的类似化合物明显降低。此外，[1,6-同型兰硫氨酸]去氨基催产素类似物的O-甲基酪氨酸或异亮氨酸在2号位置上被制备出来；这些化合物具有一定程度的催产活性。