Phe-Gly-Leu-Met-NH2*HCl | 58172-54-6

• 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: Phe-Gly-Leu-Met-NH2*HCl
• 英文别名: (2S)-N-[(2S)-1-amino-4-methylsulfanyl-1-oxobutan-2-yl]-2-[[2-[[(2S)-2-amino-3-phenylpropanoyl]amino]acetyl]amino]-4-methylpentanamide;hydrochloride
• CAS: 58172-54-6
• 化学式: C₂₂H₃₅N₅O₄S*ClH
• 分子量: 502.078
• InChiKey: KYRZIPNPLJAEFK-UVJOBNTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.35
• 重原子数：
  33.0
• 可旋转键数：
  14.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  156.41
• 氢给体数：
  5.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Phe-Gly-Leu-Met-NH2*HCl 在 N-甲基吗啉 、 盐酸 、 氯甲酸异丁酯 作用下， 以 溶剂黄146 为溶剂， 反应 3.03h， 生成
  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 The amino-acid residue of other selected places has also been replaced by Glu(OBz1) or Glu(OCH3).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-Gly-Leu-Met-NH2 在 盐酸 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.84h， 生成 Phe-Gly-Leu-Met-NH2*HCl
  参考文献：
  名称：

  Neubert; Hartrodt; Koch, Pharmazie, 1981, vol. 36, # 1, p. 10 - 12

  摘要：

  DOI：

文献信息

• Synthesis of partially modified retro-inverso substance P analogs and their biological activity
  作者：Michael Chorev、Elie Rubini、Chaim Gilon、Uri Wormser、Zvi Selinger

  DOI：10.1021/jm00356a003

  日期：1983.2

  Partial retro-inverso modification of a single peptide bond was applied to pGlu-Phe-Phe-Gly-Leu-Met-NH2 (I), a C-terminal hexapeptide analogue of the neuropeptide substance P. Two analogues with reversed peptide bonds, between the pGlu-Phe and Phe-Gly residues, were prepared, purified and characterized. The analogue gpGlu-(RS)-mPhe-Phe-Gly-Leu-Met-NH2 (II) was devoid of either agonistic or antagonistic

  单肽键的部分逆向逆向修饰应用于pGlu-Phe-Phe-Gly-Leu-Met-NH2（I），这是神经肽物质P的C端六肽类似物。两个具有反向肽键的类似物之间制备，纯化和鉴定pGlu-Phe和Phe-Gly残基。类似物gpGlu-（RS）-mPhe-Phe-Gly-Leu-Met-NH2（II）没有激动或拮抗活性。发现第二种伪肽类似物，即pGlu-Phe-gPhe-mGly-Leu-Met-NH2（III），是完全的激动剂，在豚鼠回肠测定中具有I的22％的效价。
• Kuhl; Doring; Neubert, Pharmazie, 1984, vol. 39, # 12, p. 814 - 816
  作者：Kuhl、Doring、Neubert、Jakubke

  DOI：——

  日期：——
• Analogues of substance P containing an α-hydroxy, β-amino acid: synthesis and biological activity
  作者：A Ewenson、R Laufer、M Chorev、Z Selinger、C Gilon

  DOI：10.1016/0223-5234(91)90104-u

  日期：1991.6

  Several bestatin-like analogues of pGlu6-Phe7-Phe8-Gly9-Leu10-Met11-NH2, a C-terminal hexapeptide derived from substance P (SP), an endogenous mammalian neuropeptide, were prepared. In this sequence [pGlu6]SP(6-11), Phe7 or Phe8 were substituted by the amino acid. (R,S)-alpha-hydroxy, (S)-beta-amino, 4-phenylbutyfic acid (AHPA). Several key diastereomeric products were resolved by selective precipitation from the reaction mixture and the resolved components were characterized by chromatography. FAB-mass spectrometry and amino acid analysis. The inhibitory potency of these peptides on SP degradation in rat diencephalon preparations was assayed. It was found that one of the resolved diastereomeric analogues, [pGlu6, AHPA8]SP(6-11) (9a) was a potent inhibitor of SP degradation with an IC50 of 20-mu-M. The analogues prepared in this study were devoid of spasmogenic activity on the guinea-pig ileum assay.
• Wasiak, Tadeusz; Koziolkiewicz, Wiktor, Polish Journal of Chemistry, 1983, vol. 57, # 7/8/9, p. 861 - 865
  作者：Wasiak, Tadeusz、Koziolkiewicz, Wiktor

  DOI：——

  日期：——
• JANECKA, ANNA;KOZIOLKIEWICZ, WIKTOR;WASIAK, TADEUSZ, POL. J. CHEM., 61,(1987) N 7-12, 761-765
  作者：JANECKA, ANNA、KOZIOLKIEWICZ, WIKTOR、WASIAK, TADEUSZ

  DOI：——

  日期：——