Boc-Phe-Phe-Gly-Leu-Met-NH2 | 73148-99-9

• 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-Leu-Met-NH2
• 英文别名: tert-butyl N-[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]carbamate
• CAS: 73148-99-9
• 化学式: C₃₆H₅₂N₆O₇S
• 分子量: 712.911
• InChiKey: WANSFHZXVRWNTA-DZUOILHNSA-N

物化性质

• 熔点：
  225-227 °C
• 沸点：
  1048.2±65.0 °C(Predicted)
• 密度：
  1.190±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  50
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  223
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Boc-Phe-Phe-Gly-Leu-Met-NH2 在 苯甲醚 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 pyroglutamyl-phenylalanyl-phenylalanine-glycyl-leucyl-methionine amide
  参考文献：
  名称：

  Activity of the C-terminal part of substance P on guinea pig ileum and trachea preparations I. N-acylated pentapeptides SP(7–11)

  摘要：

  DOI：

  10.1016/0223-5234(88)90006-2
• 作为产物：
  描述：

  N-tert-butoxycarbonyl-L-phenylalanine-L-phenylalanine-glycine 在 N-甲基吗啉 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 生成 Boc-Phe-Phe-Gly-Leu-Met-NH2
  参考文献：
  名称：

  Conformationally restricted C-terminal peptides of substance P. Synthesis, mass spectral analysis and pharmacological properties

  摘要：

  Four cyclic analogues of the C-terminal hepta- or hexapeptide of substance P were prepared by the solution method. The cyclizations were obtained by substituting with cysteine the residues normally present in positions 5 or 6 or 11 of substance P and by subsequent disulfide bond formation. The final products were identified by ordinary analytical procedures and advanced mass spectroscopy. The biological activities were determined on three bioassays: the guinea pig ileum, the guinea pig trachea and the rabbit mesenteric vein. Results obtained with these assays indicate that all peptides with a disulfide bridgehead in position 11 are inactive and that a cycle between positions 5 and 6 already strongly reduces the biological activity. The acyclic precursors containing thiol protection groups display weak biological activities. These results further underline the importance of the side chain in position 11 of substance P and suggest that optimal biological activities may require a linear peptide sequence.

  DOI：

  10.1021/jm00148a029

文献信息

• Kinetically Controlled Peptide Synthesis Mediated by Papain Using the Carbamoylmethyl Ester as an Acyl Donor
  作者：Toshifumi Miyazawa、Takao Horimoto、Kayoko Tanaka

  DOI：10.1007/s10989-014-9393-0

  日期：2014.9

  carbamoylmethyl (Cam) esters as acyl donors in the presence of a cysteine protease, papain, immobilized on Celite. Several segment condensations were also achieved generally in high yields without danger of racemization and formation of the secondary-hydrolysis product. Moreover, partial sequences of some bioactive peptides were prepared through segment condensations, and aimed-at peptides were obtained generally

  在固定于硅藻土的半胱氨酸蛋白酶木瓜蛋白酶存在下，通常以高收率合成一系列二肽，其中氨基甲酰基甲基（Cam）酯为酰基供体。通常也以高收率获得数个段的缩合，而没有消旋化和形成二次水解产物的危险。此外，一些生物活性肽的部分序列是通过片段缩合制备的，并且通常以高收率获得了针对性的肽，而没有羧基组分的C-末端残基的外消旋化。因此，在半胱氨酸介导的偶联中再次确定了Cam酯在动力学控制的肽合成中的优越性。 如先前报道的被丝氨酸蛋白酶催化的那些。
• Design, synthesis, and evaluation of substance P analogue with potential anti-pseudoallergic activity
  作者：Xiangjun Wang、Jiayu Lu、Ting Zhang、Shuai Ge、Yuexin Lv、Yajing Hou、Xinyue Yang、Cheng Wang、Huaizhen He

  DOI：10.1039/d1nj02751d

  日期：——

  endogenous agonist of the receptor as a competitive inhibitor through structural modifications. Substance P induces mast cell activation through the MRGPRX2. Therefore, we designed and synthesized a new substance P analogue, and a β-hexaminosidase assay and Ca2+ mobilization assay were performed to evaluate the anti-allergic effect of the substance P analogue, while its binding characteristic to MRGPRX2

  肥大细胞 (MC) 是可引起过敏反应的先天免疫细胞。假性过敏反应是一种具有过敏临床症状的反应，不涉及免疫 MC 的 IgE 途径。一些研究发现 MRGPRX2 对介导此类过敏反应至关重要，因为一些拮抗剂和激动剂具有相同的结合位点。一个有希望的方向是通过结构修饰使用受体的内源性激动剂作为竞争性抑制剂。物质 P 通过 MRGPRX2 诱导肥大细胞活化。因此，我们设计并合成了一种新的物质P类似物，以及β-己氨基苷酶测定和Ca 2+进行动员试验以评估物质P类似物的抗过敏作用，同时通过分子对接和细胞膜层析分析其与MRGPRX2的结合特性。结果表明，P 物质类似物可能是治疗假性过敏反应的潜在治疗剂。
• Lipkowski, Andrzej W.; Misicka, Aleksandra; Drabarek, Stefania, Polish Journal of Chemistry, 1981, vol. 55, # 4, p. 813 - 818
  作者：Lipkowski, Andrzej W.、Misicka, Aleksandra、Drabarek, Stefania

  DOI：——

  日期：——
• Kuhl; Doring; Neubert, Pharmazie, 1984, vol. 39, # 12, p. 814 - 816
  作者：Kuhl、Doring、Neubert、Jakubke

  DOI：——

  日期：——
• Synthesis of substance-P C-terminal hexapeptide analogues and their biological activity. Analogues with antagonistic activity without containing d-amino acids
  作者：K Karagiannis、A Manolopoulou、C Poulos、G Stavropoulos

  DOI：10.1016/0223-5234(94)90028-0

  日期：1994.1

  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.