(S)-methyl 2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate | 132438-33-6

• 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: (S)-methyl 2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate
• 英文别名: Fmoc-VL-OMe；Fmoc-Val-Leu-OMe；Methyl N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-L-leucinate；methyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]-4-methylpentanoate
• CAS: 132438-33-6
• 化学式: C₂₇H₃₄N₂O₅
• 分子量: 466.577
• InChiKey: OHQUVDKQWKRCQK-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-methyl 2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate 在 三氯化铝 、 N,N-二甲基苯胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 生成 methyl L-valyl-L-leucinate
  参考文献：
  名称：

  在 AlCl3/N,N-二甲基苯胺试剂系统中通过调节摩尔比对 N-Fmoc-氨基酸和 N-Fmoc-二肽甲酯的 α-氨基和羧基官能团进行选择性和化学选择性脱保护

  摘要：

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  DOI：

  10.1002/ejoc.200400321
• 作为产物：
  描述：

  FMOC-L-缬氨酸羟基琥珀酰亚胺酯 在 sodium hydrogen sulfide 、 copper(ll) sulfate pentahydrate 作用下， 以 甲醇 为溶剂， 反应 4.08h， 生成 (S)-methyl 2-((S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-methylbutanamido)-4-methylpentanoate
  参考文献：
  名称：

  Copper(ii) mediated facile and ultra fast peptide synthesis in methanol

  摘要：

  描述了一种新颖的、超快速的、温和且可扩展的氨基键形成策略，该策略在甲醇中使用简单的硫酸和胺。机制表明，偶联反应最初由硫酸铜·5水合物介导，随后由原位生成的硫化铜催化。纯肽的分离在不到5分钟的时间内获得了令人满意的产率。

  DOI：

  10.1039/c2cc32581k

文献信息

• Alternative and Chemoselective Deprotection of the ?-Amino and Carboxy Functions ofN-Fmoc-Amino Acid andN-Fmoc-Dipeptide Methyl Esters by Modulation of the Molar Ratio in the AlCl3/N,N-Dimethylaniline Reagent System
  作者：Maria�Luisa Di Gioia、Antonella Leggio、Adolfo Le Pera、Angelo Liguori、Francesca Perri、Carlo Siciliano

  DOI：10.1002/ejoc.200400321

  日期：2004.11

  The amino and carboxy functions in N-Fmoc-α-amino acid and N-Fmoc-peptide methyl esters can be alternatively and chemoselectively deprotected by treatment with the reagent system AlCl3/N,N-dimethylaniline (DMA). The chemoselectivity of the process is controlled by modulating the relative molar ratio of the Lewis acid and DMA. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)

  N-Fmoc-α-氨基酸和 N-Fmoc-肽甲酯中的氨基和羧基官能团可以通过使用试剂系统 AlCl3/N,N-二甲基苯胺 (DMA) 进行选择性化学选择性脱保护。该过程的化学选择性是通过调节路易斯酸和 DMA 的相对摩尔比来控制的。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)
• Biocatalytic induction of supramolecular order
  作者：Andrew R. Hirst、Sangita Roy、Meenakshi Arora、Apurba K. Das、Nigel Hodson、Paul Murray、Stephen Marshall、Nadeem Javid、Jan Sefcik、Job Boekhoven、Jan H. van Esch、Stefano Santabarbara、Neil T. Hunt、Rein V. Ulijn

  DOI：10.1038/nchem.861

  日期：2010.12

  Supramolecular gels, which demonstrate tunable functionalities, have attracted much interest in a range of areas, including healthcare, environmental protection and energy-related technologies. Preparing these materials in a reliable manner is challenging, with an increased level of kinetic defects observed at higher self-assembly rates. Here, by combining biocatalysis and molecular self-assembly, we have shown the ability to more quickly access higher-ordered structures. By simply increasing enzyme concentration, supramolecular order expressed at molecular, nano- and micro-levels is dramatically enhanced, and, importantly, the gelator concentrations remain identical. Amphiphile molecules were prepared by attaching an aromatic moiety to a dipeptide backbone capped with a methyl ester. Their self-assembly was induced by an enzyme that hydrolysed the ester. Different enzyme concentrations altered the catalytic activity and size of the enzyme clusters, affecting their mobility. This allowed structurally diverse materials that represent local minima in the free energy landscape to be accessed based on a single gelator structure. Supramolecular gels show promise in diverse areas, including healthcare and energy technologies, owing to tunable properties that arise directly from the organization of their building blocks. Researchers have now been able to control this behaviour by combining enzymatic catalysis with molecular self-assembly. Although it seems counter-intuitive, gels that assembled faster showed fewer defects.

  超分子凝胶具有可调功能，在医疗保健、环境保护和能源相关技术等多个领域备受关注。以可靠的方式制备这些材料具有挑战性，因为在较高的自组装速率下会观察到更多的动力学缺陷。在这里，通过将生物催化与分子自组装相结合，我们展示了更快获得更高有序结构的能力。只需增加酶的浓度，分子、纳米和微米级的超分子有序性就会显著增强，重要的是，凝胶剂的浓度保持不变。双亲分子的制备方法是在二肽骨架上连接一个芳香分子，并以甲酯封顶。它们的自组装是由一种水解酯的酶诱导的。不同浓度的酶会改变酶簇的催化活性和大小，从而影响其流动性。这样，就可以根据单一凝胶体结构获得结构多样的材料，这些材料代表了自由能图谱中的局部最小值。超分子凝胶在医疗保健和能源技术等多个领域都大有可为，因为其可调特性直接来源于其构建模块的组织。现在，研究人员已经能够通过将酶催化与分子自组装相结合来控制这种行为。虽然这似乎有违直觉，但组装速度更快的凝胶显示出更少的缺陷。
• Sureshbabu, Vommina V.; Venkataramanarao, Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 6, p. 910 - 919
  作者：Sureshbabu, Vommina V.、Venkataramanarao, Rao

  DOI：——

  日期：——
• Copper(ii) mediated facile and ultra fast peptide synthesis in methanol
  作者：Sachitanand M. Mali、Sandip V. Jadhav、Hosahudya N. Gopi

  DOI：10.1039/c2cc32581k

  日期：——

  A novel, ultrafast, mild and scalable amide bond formation strategy in methanol using simple thioacids and amines is described. The mechanism suggests that the coupling reactions are initially mediated by CuSO4·5H2O and subsequently catalyzed by in situ generated copper sulfide. The pure peptides were isolated in satisfactory yields in less than 5 minutes.

  描述了一种新颖的、超快速的、温和且可扩展的氨基键形成策略，该策略在甲醇中使用简单的硫酸和胺。机制表明，偶联反应最初由硫酸铜·5水合物介导，随后由原位生成的硫化铜催化。纯肽的分离在不到5分钟的时间内获得了令人满意的产率。