Boc-Phe-Phe-Gly-OBzl | 64698-97-1

• 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: Boc-Phe-Phe-Gly-OBzl
• CAS: 64698-97-1
• 化学式: C₃₂H₃₇N₃O₆
• 分子量: 559.662
• InChiKey: JPDGNINPUJKJHT-SVBPBHIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.71
• 重原子数：
  41.0
• 可旋转键数：
  12.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  122.83
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Phe-Gly-OBzl 在 palladium on activated charcoal 氢气 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-tert-butoxycarbonyl-L-phenylalanine-L-phenylalanine-glycine
  参考文献：
  名称：

  Synthesis of substance-P C-terminal hexapeptide analogues and their biological activity. Analogues with antagonistic activity without containing d-amino acids

  摘要：

  Analogues of the C-terminal hexapeptide of substance P have been synthesized in which each amino-acid residue was replaced by the bulky and strong lipophilic residue Asp(OBz1). The amino-acid residue of other selected places has also been replaced by Glu(OBz1) or Glu(OCH3). The resulting analogues were assayed for agonistic and antagonistic activity in 3 biological preparations, GPI, RC and RPV, which have been proposed as representative of the NK-1, NK-2 and NK-3 receptors, respectively. Although none of the analogues contained D-amino acids, they showed antagonistic activity according to the receptor type. Structure-activity relationships are also reported.

  DOI：

  10.1016/0223-5234(94)90028-0
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 在 N-甲基吗啉 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 26.25h， 生成 Boc-Phe-Phe-Gly-OBzl
  参考文献：
  名称：

  通过吡啶环合成仿生全合成吡啶酯 A2

  摘要：

  报道了含吡啶大环肽pyritide A2的化学合成。受生物合成的启发，生物合成通过翻译后修饰肽的环加成进行，所描述的方法的特点是直接从简单的氨基酸前体快速合成三取代的吡啶。事实证明，该策略对于制备与此类天然产物相关的不同吡啶是通用的。

  DOI：

  10.1002/anie.202212299

文献信息

• Synthesis and biological activity of substance P C-terminal hexapeptide analogues: structure-activity studies
  作者：Constantine Poulos、John R. Brown、Christopher C. Jordan

  DOI：10.1021/jm00157a028

  日期：1986.7

  series of analogues of the C-terminal hexapeptide of substance P, modified at the glutaminyl residue, was synthesized and their relative activities as spasmogens were determined in the guinea pig ileum and rat colon muscularis mucosae preparations in vitro. In general, when compared to SP6-11, the loss of the carboxamide group has little effect on activity in the colon and reduces activity on the ileum

  合成了一系列在谷氨酰胺残基上修饰的物质P的C端六肽类似物，并在体外确定了豚鼠回肠和大鼠结肠粘膜黏膜制剂中作为痉挛源的相对活性。通常，与SP6-11相比，羧酰胺基的丢失对结肠的活性影响很小，而对回肠的活性降低。例外的是Orn6类似物，它在两种制剂中均具有活性，被提议作为结构活性研究的有用工具。结论是6位取代基的氢键电势可能是生物活性的重要决定因素。
• Synthesis of substance P analogs with arginine in position eleven.
  作者：SHOSUKE SOFUKU、KEISUKE TORIGOE、ICHIRO MURAMATSU

  DOI：10.1248/cpb.32.4144

  日期：——

  Substance P analogs, [Arg11]-SP and SP (1-10)-Arg-OH, were synthesized by the liquid phase method. These peptides were purified by ion-exchange chromatography and partition chromatography. The biological activity of the peptides was evaluated in vitro on guinea-pig ileum. Replacement of Met11 in SP with Arg diminished the potency of SP activity. The analogs were found to be inactive as antagonists.

  物质P类似物[Arg11]-SP和SP (1-10)-Arg-OH通过液相法合成。通过离子交换色谱和分配色谱对这些肽进行了纯化。肽的生物活性在体外用豚鼠回肠进行了评估。在SP中用Arg替代Met11降低了SP的活性效能。这些类似物被发现作为拮抗剂是无活性的。
• Neubert; Hartrodt; Mehlis, Pharmazie, 1985, vol. 40, # 8, p. 532 - 535
  作者：Neubert、Hartrodt、Mehlis、Rueger、Bergmann、Lindau、Jakubke、Barth

  DOI：——

  日期：——