(-) H-Pro-Leu-OMe*HCl | 77935-35-4

• 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: (-) H-Pro-Leu-OMe*HCl
• 英文别名: methyl L-proline-L-leucinate hydrochloride；Pro-Leu-OMe hydrochloride；methyl (2S)-4-methyl-2-[[(2S)-pyrrolidine-2-carbonyl]amino]pentanoate;hydrochloride
• CAS: 77935-35-4
• 化学式: C₁₂H₂₂N₂O₃*ClH
• 分子量: 278.779
• InChiKey: MJWWHSKDMAFSLC-IYPAPVHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.86
• 重原子数：
  18.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  67.43
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-) H-Pro-Leu-OMe*HCl 、 在 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 生成 methyl 3-phenyl-(3S,2R)-oxy-glycyl-L-proline-L-leucinate
  参考文献：
  名称：

  Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of N-Cinnamoyl l-Proline Derived Peptides

  摘要：

  A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high pi-facial selectivity during these epoxidations. The origin of this diastereo-selectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d(6), and CH3CN medium and (ii) existence of these peptides as organized structures (gamma- and beta-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high pi-facial selectivity is due to the well-defined gamma- and beta-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.

  DOI：

  10.1021/jo020352j

文献信息

• π-Facial selectivity in polyaniline supported cobalt catalysed aerobic epoxidation of N-cinnamoyl proline derivatives
  作者：E.N Prabhakaran、Jyoti Prokash Nandy、Shalini Shukla、Javed Iqbal

  DOI：10.1016/s0040-4039(00)01949-3

  日期：2001.1

  Polyaniline supported cobalt salen catalyses the facially selective aerobic epoxidation (oxygen/2-methylpropanal) of N-cinnamoyl proline derived peptides. A high diastereoselectivity is observed for peptides which are able to adopt a gamma- or beta -turn due to intramolecular hydrogen bonding. (C) 2000 Elsevier Science Ltd. Ail rights reserved.
• Conformation control of bilatrienes by peptides: A survey
  作者：Daniel Krois、Harald Lehner

  DOI：10.1007/bf00815170

  日期：——

  A variety of bilipeptides has been synthesized and investigated by UV-VIS and CD spectroscopy to explore the conformational influence of peptide ligands on the covalently bound tetrapyrrol moiety. The results obtained are complemented by those reported previously. From the comprehensive data thus available several features of the peptide chain regulating interactions with the bilatriene moiety have been elucidated. Accordingly, the presence of three amide linkages at the ligand is prerequiste for induction of pronounced conformational changes consisting either in a complete transition of M into P helical bilatriene species by inversion of all torsional angles, or in a stretching of the chromophore. The kind of conformational influence can be controlled by varying the position of the prolyl entity within a given peptide.
• KROIS, DANIEL;LEHNER, HARALD, MONATSH. CHEM., 122,(1991) N-2, C. 89-100
  作者：KROIS, DANIEL、LEHNER, HARALD

  DOI：——

  日期：——