Boc-Pro-Ile-OBzl | 103725-76-4

• 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: Boc-Pro-Ile-OBzl
• 英文别名: Boc-L-Pro-L-Ile-OBz；Boc-Pro-Ile-Bzl
• CAS: 103725-76-4
• 化学式: C₂₃H₃₄N₂O₅
• 分子量: 418.533
• InChiKey: SMPVADVOZQOBJF-WDSOQIARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.66
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Boc-Pro-Ile-OBzl 在 palladium on activated charcoal 氢气 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 L-prolyl-L-phenylalanyl-L-prolylglycyl-L-prolyl-L-isoleucine
  参考文献：
  名称：

  Structure of Halo-toxin Produced by Phytopathogenic Bacterium,Pseudomonas syringaepv.mori

  摘要：

  从导致桑树叶子出现光环亮病的铵根桿菌（Pseudomonas syringae pv. mori）培养基中分离出了光环毒素。通过光谱手段和氨基酸序列分析，该化合物的结构被揭示为Pro-Phe-Pro-Gly-Pro-Ile。

  DOI：

  10.1246/cl.1989.679
• 作为产物：
  描述：

  BOC-L-脯氨酸 、 L-异亮氨酸,苯基甲基酯,盐酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以90%的产率得到Boc-Pro-Ile-OBzl
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Vinca Alkaloids and Phomopsin Hybrids

  摘要：

  Ten hybrids of vinca alkaloids and phomopsin A have been synthesized by linking the octahydrophomopsin lateral chain to the tertiary amine of the cleavamine moiety of anhydrovinblastine (AVLB) and vinorelbine. These compounds have been elaborated in order to obtain original products that may interfere with both binding sites of vinblastine (VLB) and phomopsin in tubulin. Although NMR and molecular modeling studies have shown that the orientation of the added peptide chains of these hybrids is not the same as those of phomopsin A, most of them are very potent inhibitors of microtubules assembly and they present good cytotoxicity against KB cell line. These interesting biological activities may eventually be explained by the fact that their lateral chain resides in a pocket distinct from that of the phomopsin A peptide, at the interface of tubulins beta and alpha.

  DOI：

  10.1021/jm801064y

文献信息

• Molecular Capture and Conformational Change of Diketopiperazines Containing Proline Residues by Epigallocatechin-3-<i>O</i>-gallate in Water
  作者：Takashi Ishizu、Miku Tokunaga、Moeka Fukuda、Mana Matsumoto、Takeshi Goromaru、Soushi Takemoto

  DOI：10.1248/cpb.c21-00047

  日期：2021.6.1

  hydrophobicity of the side chain of the amino acid residue of cyclo(Pro-Xxx) led to a higher molecular capture ability. Furthermore, the molecular capture ability decreased when the side chain of the amino acid residue had a hydrophilic hydroxyl group. When diketopiperazine cyclo(Pro-Xxx), excluding cyclo(D-Pro-L-Ala), was taken into the hydrophobic space formed by the three aromatic A, B, and B′ rings of EGCg

  将二酮哌嗪环（Pro-Xxx）（Xxx：氨基酸残基）的水溶液添加到（-）-表没食子儿茶素-3- O的水溶液中-gallate (EGCg) 导致 EGCg 和环 (Pro-Xxx) 的复合物沉淀。使用 EGCg 的环 (Pro-Xxx) 的分子捕获能力通过与 EGCg 复合物的沉淀物中包含的环 (Pro-Xxx) 的量与所用的总环 (Pro-Xxx) 的量之比来评估。cyclo(Pro-Xxx) 氨基酸残基侧链的更强疏水性导致更高的分子捕获能力。此外，当氨基酸残基的侧链具有亲水性羟基时，分子捕获能力降低。当不包括环(D-Pro-L-Ala)的二酮哌嗪环(Pro-Xxx)被带入EGCg的三个芳香A、B和B'环形成的疏水空间中，形成复合物时，它们的构象保持在疏水空间中。基于核奥弗豪泽效应 (NOE) 测量，2 O 是轴向的，而环（L-Pro-L-Ala）是赤道的。当环(D-Pro-L-Ala)
• Synthesis of Pro-Pro-Ile, a corticoliberin fragment, labeled with tritium in proline unit
  作者：V. P. Shevchenko、I. Yu. Nagaev、L. A. Andreeva、N. F. Myasoedov

  DOI：10.1134/s1066362210030185

  日期：2010.6

  Boc-Delta(3)Pro-Pro-Ile-OBzl and Boc-Pro-Delta(3)Pro-Ile-OBzl were synthesized. Tritium-labeled Pro-Pro- Ile was prepared by their hydrogenation in a tritium atmosphere in the presence of a catalyst. In the reduction of Boc-Delta(3)Pro-Pro-Ile-OBzl and Boc-Pro-Delta(3)Pro-Ile-OBzl, elimination of the Bzl protective group occurs faster than hydrogenation of the 3,4-dehydroproline residue (benzene and dioxane were used as solvents). The resulting Boc-Delta(3)Pro-Pro-Ile-OH. and Boc-Pro-Delta(3)Pro-Ile-OH. are poorly soluble in aprotic solvents, which accounts for the low yield of the desired tritium-labeled peptides.