Boc-Pro-(4S)Azp-OMe | 1251461-98-9

• 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-OMe
• 英文别名: (S)-2-((2S,4S)-4-azido-2-(methoxycarbonyl)pyrrolidine-1-carbonyl)pyrrolidine-1-carboxylate
• CAS: 1251461-98-9
• 化学式: C₁₆H₂₅N₅O₅
• 分子量: 367.405
• InChiKey: ZAYNXXNKRQYTKM-SRVKXCTJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.84
• 重原子数：
  26.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  124.91
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Boc-Pro-(4S)Azp-OMe 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 4.0h， 以100%的产率得到Boc-Pro-(4S)Azp-OH
  参考文献：
  名称：

  Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

  摘要：

  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。

  DOI：

  10.1039/c8cc05588b
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 在 sodium azide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 Boc-Pro-(4S)Azp-OMe
  参考文献：
  名称：

  Design and synthesis of galactose-conjugated fluorinated and non-fluorinated proline oligomers: towards antifreeze molecules

  摘要：

  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。

  DOI：

  10.1039/c8cc05588b

文献信息

• Altering the Sex Pheromone Cyclo(l-Pro-l-Pro) of the Diatom Seminavis robusta towards a Chemical Probe
  作者：Eli Bonneure、Amber De Baets、Sam De Decker、Koen Van den Berge、Lieven Clement、Wim Vyverman、Sven Mangelinckx

  DOI：10.3390/ijms22031037

  日期：——

  As a major group of algae, diatoms are responsible for a substantial part of the primary production on the planet. Pennate diatoms have a predominantly benthic lifestyle and are the most species-rich diatom group, with members of the raphid clades being motile and generally having heterothallic sexual reproduction. It was recently shown that the model species Seminavis robusta uses multiple sexual cues during mating, including cyclo(l-Pro-l-Pro) as an attraction pheromone. Elaboration of the pheromone-detection system is a key aspect in elucidating pennate diatom life-cycle regulation that could yield novel fundamental insights into diatom speciation. This study reports the synthesis and bio-evaluation of seven novel pheromone analogs containing small structural alterations to the cyclo(l-Pro-l-Pro) pheromone. Toxicity, attraction, and interference assays were applied to assess their potential activity as a pheromone. Most of our analogs show a moderate-to-good bioactivity and low-to-no phytotoxicity. The pheromone activity of azide- and diazirine-containing analogs was unaffected and induced a similar mating behavior as the natural pheromone. These results demonstrate that the introduction of confined structural modifications can be used to develop a chemical probe based on the diazirine- and/or azide-containing analogs to study the pheromone-detection system of S. robusta.

  作为藻类的一个主要群体，硅藻对地球上的初级生产负有重要责任。羽毛硅藻主要生活在底栖环境中，是种类最丰富的硅藻群体，其中拉菲德类成员具有运动能力，通常进行异配子性繁殖。最近的研究表明，模式物种Seminavis robusta在交配过程中使用多种性引诱物质，包括环状(l-Pro-l-Pro)作为一种吸引素。详细研究引诱物质检测系统是阐明羽毛硅藻生命周期调控的关键方面，可能为硅藻物种形成提供新的基础见解。本研究报告了合成和生物评价七种含有对环状(l-Pro-l-Pro)引诱物质进行小结构改变的新型引诱物质类似物。毒性、吸引力和干扰实验被应用来评估它们作为引诱物质的潜在活性。我们大部分的类似物显示出中等至良好的生物活性和低至无植物毒性。含有叠氮基和二氮烯基的类似物的引诱物质活性不受影响，并诱导了与天然引诱物质相似的交配行为。这些结果表明，引入有限的结构修饰可以用于开发基于叠氮基和/或二氮烯基类似物的化学探针，以研究S. robusta的引诱物质检测系统。
• Hybrid Bombesin Analogues: Combining an Agonist and an Antagonist in Defined Distances for Optimized Tumor Targeting
  作者：Carsten Kroll、Rosalba Mansi、Friederike Braun、Stefanie Dobitz、Helmut R. Maecke、Helma Wennemers

  DOI：10.1021/ja4087648

  日期：2013.11.13

  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.
• 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.