Fmoc-Arg(Pbf)-NHBn | 1408237-85-3

• 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: Fmoc-Arg(Pbf)-NHBn
• CAS: 1408237-85-3
• 化学式: C₄₁H₄₇N₅O₆S
• 分子量: 737.92
• InChiKey: GXPGYIXESONSQU-DHUJRADRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  53.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  158.71
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Arg(Pbf)-NHBn 在 N-甲基吗啉 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Development of a Peptidomimetic Antagonist of Neuropeptide FF Receptors for the Prevention of Opioid-Induced Hyperalgesia

  摘要：

  Through the development of a new class of unnatural ornithine derivatives as bioisosteres of arginine, we have designed an orally active peptidomimetic antagonist of neuropeptide FF receptors (NPFFR). Systemic low-dose administration of this compound to rats blocked opioid-induced hyperalgesia, without any apparent side-effects. Interestingly, we also observed that this compound potentiated opioid-induced analgesia. This unnatural ornithine derivative provides a novel therapeutic approach for both improving analgesia and reducing hyperalgesia induced by opioids in patients being treated for chronic pain.

  DOI：

  10.1021/cn500219h
• 作为产物：
  描述：

  苄胺 、 Fmoc-Pbf-L-精氨酸 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以97%的产率得到Fmoc-Arg(Pbf)-NHBn
  参考文献：
  名称：

  A study on the induction of stereoselectivity in the Strecker synthesis of basic amino acid-derived α-amino nitriles

  摘要：

  Diverse basic amino acid-derived alpha-amino nitriles have been synthesized via a modified Strecker reaction, using TMSCN as the cyanide source. It has been found that this synthesis is a slow thermodynamically controlled reaction, where it was difficult to induce stereocontrol. Moderate selectivity was induced by thermodynamic control of the reaction in MeOH. The absolute configuration at the stereogenic center generated was assigned by chemical correlation with 2-oxopiperazine derivatives. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2012.07.009