(2S,3S)-2,3-dibenzoyloxybutanedioic acid;methyl (1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylate | 110769-85-2

• 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: (2S,3S)-2,3-dibenzoyloxybutanedioic acid;methyl (1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylate
• CAS: 110769-85-2
• 化学式: C₁₁H₁₃NO₂*C₁₈H₁₄O₈
• 分子量: 549.534
• InChiKey: VNPAHRSIRFTVNI-PYJFVIANSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.65
• 重原子数：
  40.0
• 可旋转键数：
  9.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  179.52
• 氢给体数：
  3.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2S,3S)-2,3-dibenzoyloxybutanedioic acid;methyl (1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylate 在 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.75h， 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：

  trans-1-ethyl oxycarbonyl-2-phenylcyclopropanecarboxylic acid 在 盐酸 、 硫酸 、 三乙胺 、 sodium hydroxide 、 sodium nitrite 作用下， 以 四氢呋喃 、 乙醇 、 水 、 乙酸乙酯 为溶剂， 反应 47.0h， 生成 (2S,3S)-2,3-dibenzoyloxybutanedioic acid;methyl (1R,2R)-1-amino-2-phenylcyclopropane-1-carboxylate
  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

• MAPELLI, CLAUDIO;STAMMER, CHARLES H.;LOK, STAN;MIERKE, DALE F.;GOODMAN, M+, INT. J. PEPTIDE AND PROTEIN RES., 32,(1988) N, C. 484-495
  作者：MAPELLI, CLAUDIO、STAMMER, CHARLES H.、LOK, STAN、MIERKE, DALE F.、GOODMAN, M+

  DOI：——

  日期：——