Fmoc-Pro-(4S)Azp-Pro-OH | 1381777-66-7

• 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: Fmoc-Pro-(4S)Azp-Pro-OH
• 英文别名: (2S)-1-[(2S,4S)-4-azido-1-[(2S)-1-(9H-fluoren-9-ylmethoxycarbonyl)pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carboxylic acid
• CAS: 1381777-66-7
• 化学式: C₃₀H₃₂N₆O₆
• 分子量: 572.621
• InChiKey: KEHPKXSPMSGZNY-UZTPZCRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  42
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  122
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Fmoc-Pro-(4S)Azp-Pro-OH 、 在 tetrakis(actonitrile)copper(I) hexafluorophosphate 作用下， 以 N-甲基吡咯烷酮 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Hybrid Bombesin Analogues: Combining an Agonist and an Antagonist in Defined Distances for Optimized Tumor Targeting

  摘要：

  Radiolabeled hybrid ligands with defined distances between an agonist and an antagonist for the gastrin-releasing peptide receptor were found to have excellent tumor-targeting properties. Oligoprolines served as rigid scaffolds that allowed for tailoring distances of 10, 20, and 30 angstrom between the recognition elements. In vitro and in vivo studies revealed that the hybrid ligand with a distance of 20 angstrom between the recognition elements exhibits the highest yet observed tumor cell uptake and retention time in prostate cancer cells.

  DOI：

  10.1021/ja4087648
• 作为产物：
  描述：

  Boc-Pro-(4S)Azp-OH 在 盐酸 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 lithium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 生成 Fmoc-Pro-(4S)Azp-Pro-OH
  参考文献：
  名称：

  Hybrid Bombesin Analogues: Combining an Agonist and an Antagonist in Defined Distances for Optimized Tumor Targeting

  摘要：

  Radiolabeled hybrid ligands with defined distances between an agonist and an antagonist for the gastrin-releasing peptide receptor were found to have excellent tumor-targeting properties. Oligoprolines served as rigid scaffolds that allowed for tailoring distances of 10, 20, and 30 angstrom between the recognition elements. In vitro and in vivo studies revealed that the hybrid ligand with a distance of 20 angstrom between the recognition elements exhibits the highest yet observed tumor cell uptake and retention time in prostate cancer cells.

  DOI：

  10.1021/ja4087648

文献信息

• Oligoprolines as Scaffolds for the Formation of Silver Nanoparticles in Defined Sizes: Correlating Molecular and Nanoscopic Dimensions
  作者：Grégory Upert、Francelin Bouillère、Helma Wennemers

  DOI：10.1002/anie.201107183

  日期：2012.4.23

  Metallized scaffolds: Oligoproline scaffolds that are functionalized with aldehyde groups have been shown to control the size of silver nanoparticles that are formed in the Tollens reaction. The size of the nanoparticles correlates linearly with the length of the scaffold and the oxidation of the aldehyde moieties during the reaction helps to stabilize the nanoparticles through coordination to the

  金属化的支架：已证明用醛基官能化的寡脯氨酸支架可控制Tollens反应中形成的银纳米颗粒的尺寸。纳米粒子的尺寸与支架的长度线性相关，并且在反应过程中醛基的氧化有助于通过与新形成的羧酸基团配位来稳定纳米粒子。
• Functionalizable Oligoprolines as Molecular Scaffolds
  作者：Yvonne A. Nagel、Michael Kuemin、Helma Wennemers

  DOI：10.2533/chimia.2011.264

  日期：——

  Azidoproline (Azp) containing oligoprolines are conformationally well-defined, helical molecular scaffolds that allow for facile functionalization. Within this article we describe the synthesis of Azp-containing oligoprolines and different strategies to introduce functional moieties. In addition, the influence of factors such as substituents at the y-position of proline as well as functional groups at the termini on the conformational stability of the molecular scaffolds are briefly presented.