N-acetyl-(S)-leucyl-(S)-phenylalanine | 38329-24-7

• 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: N-acetyl-(S)-leucyl-(S)-phenylalanine
• 英文别名: N-Ac-L-Leu-L-Phe-OH；Ac-L-Leu-L-Phe-OH；Ac-LF-OH；(2S)-2-[[(2S)-2-acetamido-4-methylpentanoyl]amino]-3-phenylpropanoic acid
• CAS: 38329-24-7
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: YWGLVYWQFMNBFF-GJZGRUSLSA-N

物化性质

• 沸点：
  605.5±55.0 °C(Predicted)
• 密度：
  1.150±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  95.5
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-acetyl-(S)-leucyl-(S)-phenylalanine 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 methyl (Z,4S)-4-[[(2S)-2-acetamido-4-methyl-pentanoyl]amino]-2-cyano-3-hydroxy-5-phenyl-pent-2-enoate
  参考文献：
  名称：

  Novel modifications of peptides: simple syntheses of difunctionalized enamines, enol ethers, and thioenol ethers from carboxylic acids via acylimidazole and enol phosphate intermediates

  摘要：

  DOI：

  10.1021/jo00297a008

文献信息

• The Overman rearrangement in carbohydrate chemistry: stereoselective synthesis of functionalized 3-amino-3,6-dihydro-2H-pyrans and incorporation in peptide derivatives
  作者：Ana Montero、Enrique Mann、Bernardo Herradón

  DOI：10.1016/j.tetlet.2004.11.109

  日期：2005.1

  A stereocontrolled synthesis of an unsaturated sugar bearing two amino groups (one of them masked as an azide), using an Overman rearrangement as key step, is described. This scaffold is used to prepare two peptides having aromatic fragments, which have shown activity as calpain inhibitors.

  描述了使用Overman重排作为关键步骤的立体控制合成的不饱和糖，该不饱和糖带有两个氨基（其中一个被掩盖为叠氮基）。该支架用于制备具有芳族片段的两种肽，它们已显示出作为钙蛋白酶抑制剂的活性。
• Enzyme-catalyzed peptide synthesis in biphasic aqueous-organic systems
  作者：P. Kuhl、A. Könnecke、G. Döring、H. Däumer、N.-D. Jakubke

  DOI：10.1016/s0040-4039(00)77731-8

  日期：1980.1

  A preparative protease-catalyzed peptide synthesis in biphasic aqueous-organic systems is described. This approach using both free as well as immobilized proteases as catalysts provides high yields and includes the possibility to re-utilize the enzymes.

  描述了在双相水-有机系统中制备蛋白酶催化的肽合成。使用游离的和固定的蛋白酶作为催化剂的这种方法提供了高产率，并且包括重新利用酶的可能性。
• Prohormone-substrate peptide sequence recognition by peptidylglycine α-amidating monooxygenase and its reflection in increased glycolate inhibitor potency
  作者：Kelly M. Morris、Feihua Cao、Hideki Onagi、Timothy M. Altamore、Allan B. Gamble、Christopher J. Easton

  DOI：10.1016/j.bmcl.2012.10.004

  日期：2012.12

  The interactions of nineteen peptide substrates and fifteen analogous peptidomimetic glycolate inhibitors with human peptidylglycine alpha-amidating monooxygenase (PAM) have been investigated. The substrates and inhibitors are the prohormones of calcitonin and oxytocin and their analogues. PAM both secreted into the medium by and extracted from DMS53 small lung carcinoma cells has been studied. The results show that recognition of the prooxytocin and procalcitonin peptide sequences by the enzyme extends more than four and five amino acid residues, respectively, from their C-termini. This substrate sequence recognition is mirrored by increased inhibitor potency with increased peptide length in the glycolate peptidomimetics. Substitution of the C-terminal penultimate glycine and proline residues of prooxytocin and procalcitonin and their analogues with phenylalanine increases the enzyme binding affinity. However, this changes the binding mode from one that depends on peptide sequence recognition to another primarily determined by the phenylalanine moiety, for both the substrates and analogous glycolate inhibitors. Crown Copyright (C) 2012 Published by Elsevier Ltd. All rights reserved.
• Silica gel-catalyzed Knoevenagel condensation of peptidyl cyanomethyl ketones with aromatic aldehydes and ketones. A novel Michael acceptor functionality for C-modified peptides: the benzylidene and alkylidene cyanomethyl ketone function
  作者：Denis Brillon、Gilles Sauve

  DOI：10.1021/jo00032a042

  日期：1992.3

  Simple preparation of cyanomethyl ketone derivatives 5a-5b of N-acetylphenylalanine and N-acetylleucylphenylalanine is accomplished by condensation of the corresponding activated carboxylic acids 3a-3b and the carbanion of tert-butyl cyanoacetate to give enols 4a-4b, which are then hydrolyzed and decarboxylated. These cyanomethyl ketone compounds 5a-5b are allowed to react with aromatic aldehydes and ketones in the presence of silica gel to give the Knoevenagel condensation adducts 7-18. Malononitrile, benzoylacetonitrile, and nitroacetonitrile are also reactive. These transformations can be brought about without significant epimerization.
• Modelluntersuchungen zur papainkatalysierten Peptidsynthese im w��rig-organischen Zweiphasensystem
  作者：G�nter D�ring、Peter Kuhl、Hans-Dieter Jakubke

  DOI：10.1007/bf00905471

  日期：1981.10