Fmoc-Phe-Val-OH | 223674-40-6

• 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: Fmoc-Phe-Val-OH
• 英文别名: (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-phenylpropanoyl]amino]-3-methylbutanoic acid
• CAS: 223674-40-6
• 化学式: C₂₉H₃₀N₂O₅
• 分子量: 486.568
• InChiKey: XYCBNEVVTGBUTA-UIOOFZCWSA-N

物化性质

• 熔点：
  183-186 °C (decomp)
• 沸点：
  760.3±60.0 °C(Predicted)
• 密度：
  1.239±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Fmoc-Phe-Val-OH 在 甲基三氯硅烷 、 三乙胺 作用下， 以 氯仿 为溶剂， 反应 24.0h， 生成 (5S)-5-benzyl-3-((1S)-1-carboxy-2-methylpropyl)hydantoin
  参考文献：
  名称：

  Solid phase hydantoin synthesis: An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins

  摘要：

  An efficient and direct conversion of Fmoc-protected dipeptides to hydantoins in the solid phase is described. This methodology uses MeSiCl3 in the presence of Et3N to cleave Fmoc-protected amines directly to their isocyanates. Internal cyclization of the amide on the isocyanate follows to produce the hydantoins in high purity and with no indication of racemization. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00243-9
• 作为产物：
  描述：

  N-[(1S)-2-氯-2-氧代-1-(苯甲基)乙基]-氨基甲酸-9H-芴-9-甲酯 在 三氯化铝 、 sodium carbonate 、 N,N-二甲基苯胺 作用下， 以 氯仿 、 水 为溶剂， 反应 2.0h， 生成 Fmoc-Phe-Val-OH
  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

文献信息

• <i>α-N</i>-Protected dipeptide acids: a simple and efficient synthesis via the easily accessible mixed anhydride method using free amino acids in DMSO and tetrabutylammonium hydroxide
  作者：G. Verardo、A. Gorassini

  DOI：10.1002/psc.2503

  日期：2013.5

  to find simple and efficient methods for their synthesis. For this reason, we have investigated the synthesis of α‐N‐protected dipeptide acids by reacting the easily accessible mixed anhydride of α‐N‐protected amino acids with free amino acids under different reaction conditions. The combination of TBA‐OH and DMSO has been found to be the best to overcome the low solubility of amino acids in organic

  在医学和药理学领域中，二肽的重要性已得到充分证明，并且已进行了许多努力来寻找简单有效的合成方法。因此，我们通过使易于获得的α-N混合酸酐反应，研究了α-N保护的二肽酸的合成在不同的反应条件下用游离氨基酸保护氨基酸。已经发现，TBA-OH和DMSO的组合是克服氨基酸在有机溶剂中低溶解度的最佳方法。在这些实验条件下，均相缩合反应迅速发生且没有可检测的差向异构。本方法也适用于未保护的侧链Tyr，Trp，Glu和Asp，但不适用于Lys。后一个残基能够结合两个混合酸酐分子，得到相应的异三肽。此外，已经测试了该方案对三肽和四肽合成的适用性。这种方法减少了对保护基的需求，具有成本效益，可扩展性，并产生了可用作较大肽合成的基础材料的二肽酸。
• Convenient Peptide Synthesis without Protection of <i>C</i>-Terminals
  作者：Takuya Noguchi、Naoka Tehara、Yuki Uesugi、Seunghee Jung、Nobuyuki Imai

  DOI：10.1246/cl.2012.42

  日期：2012.1.5

  Condensation of carboxylic acids 1 and 5 with unprotected α-amino acids 2 via activation by ethyl chloroformate and triethylamine proceeded effectively to afford the corresponding amides in 50–99% yields. Tripeptide 7c was obtained in 42% yield from the dipeptide 6c in a similar manner.

  羧酸1和5与未保护的α-氨基酸2在乙基氯甲酸酯和三乙胺的活化下高效缩合，以50-99%的产率得到相应的酰胺。类似地，从二肽6c中以42%的产率获得了三肽7c。
• Convenient green preparation of dipeptides using unprotected α-amino acids
  作者：Tetsuya Ezawa、Seunghee Jung、Yuya Kawashima、Takuya Noguchi、Nobuyuki Imai

  DOI：10.1016/j.tetasy.2016.11.009

  日期：2017.1

  Dipeptides and amides were obtained in high yields from N-carbobenzyloxy a-amino acids and 3-phenylpropanoic acid with unprotected a-amino acids via the corresponding mixed carbonic carboxylic anhydrides using ethyl chloroformate and triethylamine by an ecological and convenient method in which the protection of C-terminals is not needed. (C) 2016 Elsevier Ltd. All rights reserved.
• Site-Selective C(sp³)–H Functionalization of Di-, Tri-, and Tetrapeptides at the N-Terminus
  作者：Wei Gong、Guofu Zhang、Tao Liu、Ramesh Giri、Jin-Quan Yu

  DOI：10.1021/ja510233h

  日期：2014.12.3

  Although the syntheses of novel and diverse peptides rely mainly on traditional coupling using unnatural amino acids, postsynthetic modification of peptides could provide a complementary method for the preparation of nonproteinogenic peptides. Site selectivity of postsynthetic modification of peptides is usually achieved by targeting reactive moieties, such as the thiol group of cysteine or the C-2 position of tryptophan. Herein, we report the development of site-selective functionalizations of inert C(sp(3))-H bonds of N-terminal amino acids in di-, tri-, and tetrapeptides without installing a directing group. The native amino acid moiety within the peptide is used as a ligand to accelerate the C-H activation reaction. In the long run, this newly uncovered reactivity could provide guidance for developing site-selective C(sp(3))-H activation toward postsynthetic modification of a broader range of peptides.
• Hybrid Peptide-Alkoxyamine Drugs: A Strategy for the Development of a New Family of Antiplasmodial Drugs
  作者：Ange W. Embo-Ibouanga、Michel Nguyen、Lucie Paloque、Mathilde Coustets、Jean-Patrick Joly、Jean-Michel Augereau、Nicolas Vanthuyne、Raphaël Bikanga、Naomie Coquin、Anne Robert、Gérard Audran、Jérôme Boissier、Philippe Mellet、Françoise Benoit-Vical、Sylvain R. A. Marque

  DOI：10.3390/molecules29061397

  日期：——

  The emergence and spread of drug-resistant Plasmodium falciparum parasites shed a serious concern on the worldwide control of malaria, the most important tropical disease in terms of mortality and morbidity. This situation has led us to consider the use of peptide-alkoxyamine derivatives as new antiplasmodial prodrugs that could potentially be efficient in the fight against resistant malaria parasites. Indeed, the peptide tag of the prodrug has been designed to be hydrolysed by parasite digestive proteases to afford highly labile alkoxyamines drugs, which spontaneously and instantaneously homolyse into two free radicals, one of which is expected to be active against P. falciparum. Since the parasite enzymes should trigger the production of the active drug in the parasite’s food vacuoles, our approach is summarized as “to dig its grave with its fork”. However, despite promising sub-micromolar IC50 values in the classical chemosensitivity assay, more in-depth tests evidenced that the anti-parasite activity of these compounds could be due to their cytostatic activity rather than a truly anti-parasitic profile, demonstrating that the antiplasmodial activity cannot be based only on measuring antiproliferative activity. It is therefore imperative to distinguish, with appropriate tests, a genuinely parasiticidal activity from a cytostatic activity.