N-(benzyloxycarbonyl)-(2RS)-cyclopropyl-E-phenylalanine | 86014-29-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(benzyloxycarbonyl)-(2RS)-cyclopropyl-E-phenylalanine
• 英文别名: rac-(1R,2S)-1-{[(benzyloxy)carbonyl]amino}-2-phenylcyclopropane-1-carboxylic acid；(1S,2R)-2-phenyl-1-(phenylmethoxycarbonylamino)cyclopropane-1-carboxylic acid
• CAS: 86014-29-1
• 化学式: C₁₈H₁₇NO₄
• 分子量: 311.337
• InChiKey: HARMOHOOIVBXHA-QAPCUYQASA-N

物化性质

• 沸点：
  535.4±50.0 °C(Predicted)
• 密度：
  1.31±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  23.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.63
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-(2RS)-cyclopropyl-E-phenylalanine 在 茴香硫醚 、 硫酸 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 65.25h， 生成
  参考文献：
  名称：

  A formyl peptide substituted with a conformationally constrained phenylalanine residue evokes a selective immune response in human neutrophils

  摘要：

  Formyl-Met-Leu-Phe-OH (fMLP) binds to formyl peptide receptors, FPR1 and FPR2, and evokes migration and superoxide anion production in human neutrophils. To obtain a more effective and selective ligand, fMLP analogs in which the Phe residue was substituted with four isomers of cyclopropanephenylalanine were synthesized. While Z-isomer peptides induced both migration and superoxide anion production, E-isomer peptides elicited only chemotaxis. Homologous receptor desensitization experiments revealed that E-isomer peptides bound to FPR2. Although a selective agonist of chemotaxis also binds to FPR2 without increasing intracellular calcium concentration, E-isomer peptide elevated the concentration to the same level as fMLP. Understanding of mechanisms responsible for the selectivity of the reported selective agonists and rPhe-substituted analogs should prove useful for revealing the relationship between receptor-ligand interactions and biological responses of human neutrophils. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.046
• 作为产物：
  描述：

  Z-L-Ser 4-nitrobenzyl ester 在 N,N'-二环己基碳二亚胺 、 sodium hydroxide 、 copper dichloride 作用下， 以 1,4-二氧六环 、 乙醚 、 二氯甲烷 、 水 为溶剂， 反应 23.0h， 生成 N-(benzyloxycarbonyl)-(2RS)-cyclopropyl-E-phenylalanine
  参考文献：
  名称：

  A formyl peptide substituted with a conformationally constrained phenylalanine residue evokes a selective immune response in human neutrophils

  摘要：

  Formyl-Met-Leu-Phe-OH (fMLP) binds to formyl peptide receptors, FPR1 and FPR2, and evokes migration and superoxide anion production in human neutrophils. To obtain a more effective and selective ligand, fMLP analogs in which the Phe residue was substituted with four isomers of cyclopropanephenylalanine were synthesized. While Z-isomer peptides induced both migration and superoxide anion production, E-isomer peptides elicited only chemotaxis. Homologous receptor desensitization experiments revealed that E-isomer peptides bound to FPR2. Although a selective agonist of chemotaxis also binds to FPR2 without increasing intracellular calcium concentration, E-isomer peptide elevated the concentration to the same level as fMLP. Understanding of mechanisms responsible for the selectivity of the reported selective agonists and rPhe-substituted analogs should prove useful for revealing the relationship between receptor-ligand interactions and biological responses of human neutrophils. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.11.046

文献信息

• Resolution and deblocking of racemic N-(benzyloxycarbonyl)-"cyclopropylphenylalanine"
  作者：Hitoshi Kimura、Charles H. Stammer

  DOI：10.1021/jo00162a035

  日期：1983.7