Fmoc-L-Val-L-Phe-OH | 116460-34-5

• 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-L-Val-L-Phe-OH
• 英文别名: N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valyl-L-phenylalanine；Fmoc-Val-Phe-OH；(2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-methylbutanoyl]amino]-3-phenylpropanoic acid
• CAS: 116460-34-5
• 化学式: C₂₉H₃₀N₂O₅
• 分子量: 486.568
• InChiKey: DFWDPXLDFXEQAU-UIOOFZCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 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-L-Val-L-Phe-OH 在 氯化亚砜 、 sodium azide 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 0.25h， 生成 Fmoc-Val-Phe-N3
  参考文献：
  名称：

  Suresh Babu, Vommina V.; Vasanthakumar, Ganga-Ramu; Patil, Basanagoud S., Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2005, vol. 44, # 9, p. 1853 - 1858

  摘要：

  DOI：
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 lipase N 作用下， 以 水 、 丙酮 为溶剂， 以53%的产率得到Fmoc-L-Val-L-Phe-OH
  参考文献：
  名称：

  Kunz, Horst; Kowalczyk, Danuta; Braun, Peter, Angewandte Chemie, 1994, vol. 106, # 3, p. 353 - 355

  摘要：

  DOI：

文献信息

• Glutamic Acid Selective Chemical Cleavage of Peptide Bonds
  作者：Joseph M. Nalbone、Neelam Lahankar、Lyssa Buissereth、Monika Raj

  DOI：10.1021/acs.orglett.6b00317

  日期：2016.3.4

  hydrolysis of peptide bonds at glutamic acid under neutral aqueous conditions is reported. The method relies on the activation of the backbone amide chain at glutamic acid by the formation of a pyroglutamyl (pGlu) imide moiety. This activation increases the susceptibility of a peptide bond toward hydrolysis. The method is highly specific and demonstrates broad substrate scope including cleavage of various bioactive

  据报道在中性水性条件下谷氨酸上肽键的位点特异性水解。该方法依赖于通过形成焦谷氨酰基（pGlu）酰亚胺部分而在谷氨酸上激活主链酰胺链。这种活化增加了肽键对水解的敏感性。该方法是高度特异性的，并证明了广泛的底物范围，包括具有非天然氨基酸残基的各种生物活性肽的裂解，所述非天然氨基酸残基是不适合酶促水解的底物。
• General, Mild, and Metal-Free Synthesis of Phenyl Selenoesters from Anhydrides and Their Use in Peptide Synthesis
  作者：Andrea Temperini、Francesca Piazzolla、Lucio Minuti、Massimo Curini、Carlo Siciliano

  DOI：10.1021/acs.joc.7b00173

  日期：2017.5.5

  A mild, practical, and simple procedure for phenyl selenoesters synthesis from several anhydrides and diphenyl diselenide was developed. This transition-metal-free method provides a straightforward entry to storable Fmoc-amino acid selenoesters which are effective chemoselective acylating reagents. An application to oligopeptide synthesis was illustrated.

  开发了一种温和，实用和简单的方法，用于从几种酸酐和二苯基二硒化物合成苯基硒酸酯。这种无过渡金属的方法可以直接进入可存储的Fmoc-氨基酸硒酸酯，它们是有效的化学选择性酰化试剂。说明了在寡肽合成中的应用。
• An Efficient Conversion of the Carboxylic Group of <i>N</i>-Fmoc α-Amino Acids/Peptide Acids into <i>N</i>-Formamides Employing Isocyanates as Key Intermediates
  作者：N. S. Sudarshan、N. Narendra、H. P. Hemantha、Vommina V. Sureshbabu

  DOI：10.1021/jo701371k

  日期：2007.12.1

  [Graphics]Reaction of 96% formic acid with isocyanates derived from N-Fmoc alpha-amino acids/peptide acids catalyzed by DMAP has yielded a new class of stable formamides as crystalline solids which have been characterized by IR, H-1 NMR, C-13 NMR, and mass spectroscopy. Conversion of the side chain carboxylic acid of N-Fmoc-5-oxazolidinones of Asp/Glu into the N-formyl group also has been accomplished. The reaction is simple, mild, and high yielding.
• Tetraarylphosphonium Salts as Soluble Supports for the Synthesis of Small Molecules
  作者：Federica Stazi、David Marcoux、Jean-Christophe Poupon、Daniel Latassa、André B. Charette

  DOI：10.1002/anie.200700833

  日期：2007.6.25
• A protocol for racemization-free loading of Fmoc-amino acids to Wang resin
  作者：Krishnarao Sandhya、Bhagavathula Ravindranath

  DOI：10.1016/j.tetlet.2008.02.055

  日期：2008.4

  Fmoc-amino acids are conveniently and inexpensively linked to Wang resin using benzyloxybenzyl chloride resin without the problems normally associated with the traditional methods of preparation of Fmoc-amino acid loaded Wang resins, namely, low substitution, unacceptable racemization or use of expensive reagents. (C) 2008 Elsevier Ltd. All rights reserved.