Ac-Leu-D-Phe-OH | 139168-55-1

• 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: Ac-Leu-D-Phe-OH
• 英文别名: N-Ac-L-Leu-D-Phe-OH；Ac-Leu-D-Phe-H；(2R)-2-[[(2S)-2-acetamido-4-methylpentanoyl]amino]-3-phenylpropanoic acid
• CAS: 139168-55-1
• 化学式: C₁₇H₂₄N₂O₄
• 分子量: 320.389
• InChiKey: YWGLVYWQFMNBFF-LSDHHAIUSA-N

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：

  Ac-Leu-D-Phe-OH 在 甲酸 、 silica gel 、 N,N'-羰基二咪唑 作用下， 以 二氯甲烷 为溶剂， 反应 25.0h， 生成 (S)-2-Acetylamino-4-methyl-pentanoic acid [(E)-(R)-1-benzyl-3-cyano-4-(4-methoxy-phenyl)-2-oxo-but-3-enyl]-amide
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1021/jo00032a042
• 作为产物：
  描述：

  Ac-Leu-(D)-Phe-[Glc(OMOM)4-3'(S)-5'(S)(CH2OMOM)HypH]-Val-NMe2 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 生成 、 Ac-Leu-D-Phe-OH
  参考文献：
  名称：

  葡萄糖模板脯氨酸模拟物对Gramicidin S中发现的肽片段Ac-Leu-D-Phe-Pro-Val-NMe2的β-转构象的影响。

  摘要：

  合成基于四肽的β-转弯模拟物，该模拟物包含螺环葡萄糖为模板的3-羟基脯氨酸杂种Glc3'（S）-5'（R）（CH（2）OH）HypH和Glc3'（S）-5'（S）提出了（CH（2）OH）HypH作为脯氨酸模拟物。Ac-Leu-D-Phe- [Glc3'（S）-5'（R）（CH（2）OH）HypH] -Val-NMe（2）和Ac-Leu-D-Phe的基于NMR的构象分析-[Glc3'（S）-5'（S）（CH（2）OH）HypH] -Val-NMe（2）证明存在β-转弯构象。通过改变Glc3'（S）-5'（R）（CH（2）OH）HypH的5'-位置的立体化学观察到不同的转弯结构。葡萄糖保护的四肽Ac-Leu-D-Phe- [Glc（MOM）（4）3'（S）-5'（R）（CH（2）OMOM）HypH] -Val-的主要脯氨酰胺顺式异构体NMe（2）11和不受葡萄糖保护的Ac-Leu-D-Phe-

  DOI：

  10.1016/j.carres.2010.03.037

文献信息

• Large Structural Modification with Conserved Conformation:  Analysis of Δ³-Fused Aryl Prolines in Model β-Turns
  作者：Guillaume Jeannotte、William D. Lubell

  DOI：10.1021/ja0471222

  日期：2004.11.1

  For the first time, the influence of a fused Delta3-arylproline on peptide conformation has been studied by the synthesis and comparison of the conformations of peptides containing proline and pyrrolo-proline, 3 (PyPro). Pyrrolo-proline was demonstrated to be a conservative replacement for Pro in model beta-turns, 4 and 5, as shown by their similar DMSO titration curves, cis/trans-isomer populations, and NOESY spectral data. Pyrrolo-proline may thus be used for studying the structure activity relationships of Pro-containing peptides with minimal modification of secondary structures.
• 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.
• Influence of glucose-templated proline mimetics on the β-turn conformation of the peptide fragment Ac-Leu-d-Phe-Pro-Val-NMe2 found in Gramicidin S
  作者：Kaidong Zhang、Frank Schweizer

  DOI：10.1016/j.carres.2010.03.037

  日期：2010.6

  tetrapeptide-based beta-turn mimetics containing spirocyclic glucose-templated 3-hydroxyproline hybrids Glc3'(S)-5'(R)(CH(2)OH)HypH and Glc3'(S)-5'(S)(CH(2)OH)HypH as proline mimetics is presented. NMR-based conformational analysis of Ac-Leu-D-Phe-[Glc3'(S)-5'(R)(CH(2)OH)HypH]-Val-NMe(2) and Ac-Leu-D-Phe-[Glc3'(S)-5'(S)(CH(2)OH)HypH]-Val-NMe(2) demonstrates the presence of beta-turn conformations. Different turn

  合成基于四肽的β-转弯模拟物，该模拟物包含螺环葡萄糖为模板的3-羟基脯氨酸杂种Glc3'（S）-5'（R）（CH（2）OH）HypH和Glc3'（S）-5'（S）提出了（CH（2）OH）HypH作为脯氨酸模拟物。Ac-Leu-D-Phe- [Glc3'（S）-5'（R）（CH（2）OH）HypH] -Val-NMe（2）和Ac-Leu-D-Phe的基于NMR的构象分析-[Glc3'（S）-5'（S）（CH（2）OH）HypH] -Val-NMe（2）证明存在β-转弯构象。通过改变Glc3'（S）-5'（R）（CH（2）OH）HypH的5'-位置的立体化学观察到不同的转弯结构。葡萄糖保护的四肽Ac-Leu-D-Phe- [Glc（MOM）（4）3'（S）-5'（R）（CH（2）OMOM）HypH] -Val-的主要脯氨酰胺顺式异构体NMe（2）11和不受葡萄糖保护的Ac-Leu-D-Phe-