Boc-Pro-(4S)Azp-OH | 1251461-99-0

• 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: Boc-Pro-(4S)Azp-OH
• 英文别名: (2S,4S)-4-azido-1-((tert-butoxycarbonyl)-L-prolyl)pyrrolidine-2-carboxylic acid
• CAS: 1251461-99-0
• 化学式: C₁₅H₂₃N₅O₅
• 分子量: 353.378
• InChiKey: LLTKFPGBWCDKSP-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.75
• 重原子数：
  25.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  135.91
• 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-(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
• 作为产物：
  描述：

  methyl (2S,4S)-4-azidopyrrolidine-2-carboxylate hydrochloride 在 4-二甲氨基吡啶 、 二碳酸二叔丁酯 、 lithium hydroxide 作用下， 生成 Boc-Pro-(4S)Azp-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

• Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules
  作者：Yuji Sumii、Hayata Hibino、Ibrayim Saidalimu、Hidehisa Kawahara、Norio Shibata

  DOI：10.1039/c8cc05588b

  日期：——

  Galactose-conjugated fluorinated and non-fluorinated proline oligomers were synthesized and evaluated as antifreeze molecules.

  用半乳糖偶联的氟化和非氟化脯氨酸寡聚体被合成并作为抗冻分子进行评估。
• 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.
• Functionalizable Collagen Model Peptides
  作者：Roman S. Erdmann、Helma Wennemers

  DOI：10.1021/ja103392t

  日期：2010.10.13

  The functionalizability and conformational properties of azidoproline (Azp)-containing collagen model peptides (CMPs) were studied. The results show that (4R)Azp has a similar stabilizing effect on the collagen triple helix as (4R)hydroxyproline and that functionalized CMPs are readily accessible by "click" chemistry. The resulting triazole-functionalized CMPs form stable triple helices, demonstrating that sterically demanding moieties in three symmetry-related positions in all strands are tolerated. The straightforward synthesis and facile functionalizability of the Azp-containing CMPs are intriguing for the development of functional collagen-based materials.