N-9-fluorenylmethoxycarbonyl-(2S)-prolyl-(2S)-4,4-difluoroprolylglycine | 1187430-33-6

• 英文名称: N-9-fluorenylmethoxycarbonyl-(2S)-prolyl-(2S)-4,4-difluoroprolylglycine
• 英文别名: Fmoc-Pro-Dfp-Gly-OH
• CAS: 1187430-33-6
• 化学式: C₂₇H₂₇F₂N₃O₆
• 分子量: 527.525
• InChiKey: IFZSULNSDMEZGI-VXKWHMMOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.84
• 重原子数：
  38.0
• 可旋转键数：
  6.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  116.25
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  Fmoc-Pro-Dfp-Gly-OBn 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以39%的产率得到N-9-fluorenylmethoxycarbonyl-(2S)-prolyl-(2S)-4,4-difluoroprolylglycine
  参考文献：
  名称：

  Origin of the stability conferred upon collagen by fluorination

  摘要：

  According to a prevailing theory, (2S, 4R)-4-hydroxyproline (Hyp) residues stabilize the collagen triple helix via a stereoelectronic effect that preorganizes appropriate backbone torsion angles for triple-helix formation. This theory is consistent with the marked stability that results from replacing the hydroxyl group with the more electron-withdrawing fluoro group, as in (2S, 4R)-4-fluoroproline (Flp). Nonetheless, the hyperstability of triple helices containing Flp has been attributed by others to the hydrophobic effect rather than a stereoelectronic effect. We tested this hypothesis by replacing Hyp with 4,4-difluoroproline (Dfp) in collagen-related peptides. Dfp retains the hydrophobicity of Flp, but lacks the ability of Flp to pre-organize backbone torsion angles. Unlike Flp, Dfp does not endow triple helices with elevated stability, indicating that the hyperstability conferred by Flp is not due to the hydrophobic effect. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.168