(3S)-3-氨基-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-氨基-1-氧代己烷-2-基]氨基]-4-甲基-1-氧代戊烷-2-基]氨基]-2-氧代乙基]氨基]-3-甲基-1-氧代丁烷-2-基]氨基]-1-氧代-3-苯基丙烷-2-基]氨基]-3-羟基-1-氧代丙烷-2-基]氨基]-4-氧代丁酸 | 110863-33-7

• 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
• 中文名称: (3S)-3-氨基-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-氨基-1-氧代己烷-2-基]氨基]-4-甲基-1-氧代戊烷-2-基]氨基]-2-氧代乙基]氨基]-3-甲基-1-氧代丁烷-2-基]氨基]-1-氧代-3-苯基丙烷-2-基]氨基]-3-羟基-1-氧代丙烷-2-基]氨基]-4-氧代丁酸
• 英文名称: 10>neurokinin A(4-10)
• 英文别名: 10> NKA (4-10)；[NLe¹⁰]-neurokinin A(4-10)；[Nle¹⁰] neurokinin A(4-10)；[Nle¹⁰]neurokinin A(4-10)；Asp-Ser-Phe-Val-Gly-Leu-Nle-NH2；[Nle¹⁰]-NKA(4-10)；Neurokinin A (4-10), nle(10)-；(3S)-3-amino-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-amino-1-oxohexan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-methyl-1-oxobutan-2-yl]amino]-1-oxo-3-phenylpropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-4-oxobutanoic acid
• CAS: 110863-33-7
• 化学式: C₃₅H₅₆N₈O₁₀
• 分子量: 748.877
• InChiKey: UYMRFLAHRMRHGI-WTWMNNMUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  53
• 可旋转键数：
  24
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  301
• 氢给体数：
  10
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  BOC-甘氨酸 、 N-Boc-L-缬氨酸 、 BOC-L-亮氨酸 、 N-Boc-L-正亮氨酸 、 alkaline earth salt of/the/ methylsulfuric acid 生成 (3S)-3-氨基-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-氨基-1-氧代己烷-2-基]氨基]-4-甲基-1-氧代戊烷-2-基]氨基]-2-氧代乙基]氨基]-3-甲基-1-氧代丁烷-2-基]氨基]-1-氧代-3-苯基丙烷-2-基]氨基]-3-羟基-1-氧代丙烷-2-基]氨基]-4-氧代丁酸
  参考文献：
  名称：

  Importance of the Aromatic Residue at Position 6 of [Nle¹⁰]Neurokinin A(4−10) for Binding to the NK-2 Receptor and Receptor Activation

  摘要：

  Steric and electrostatic requirements at position 6 of [Nle(10)]NKA(4-10), a full agonist of NK-2 receptors, for molecular recognition by the receptor were studied. Two series of peptide analogues, (a) p-substituted analogues, [p-X-Phe(6),Nle(10)]NKA(4-10), where X = F, Cl, Br, I, NH2, NO2, and (b) [D-Phe(6),Nle(10)]NKA(4-10), [Trp(6),Nle(10)]NKA(4-10), and [Chex-Ala(6),Nle(10)]NKA(4-10), were synthesized, and their biological activity was examined. Competition binding experiments with [H-3]NKA were performed using cloned human NK-2 receptors expressed in CHO cells. Antagonistic and agonistic properties of the analogues were studied using an in vitro functional assay with hamster tracheal rings. The rank order of potency of agonists was [Nle(10)]NKA(4-10) approximate to [p-F-Phe(6),Nle(10)]NKA(4-10) > [p-NH2-Phe(6),Nle(10)]NKA(4-10) > [p-Cl-Phe(6),Nle(10)]NKA(4-10) > [p-NO2-Phe(6),Nle(10)]NKA(4-10) > [Trp(6),Nle(10)]NKA(4-10). Size and planarity of the aromatic side chain were crucially important for the biological activity, whereas electran-donating and electron-withdrawing properties of the para-substituent were less important;. The results favor the hypothesis that weakly polar pi-pi interactions exist between the aromatic group and the receptor.

  DOI：

  10.1021/jm9807151

文献信息

• Importance of the Aromatic Residue at Position 6 of [Nle¹⁰]Neurokinin A(4−10) for Binding to the NK-2 Receptor and Receptor Activation
  作者：Dmitry S. Gembitsky、Mark Murnin、Ferenc L. Ötvös、James Allen、Richard F. Murphy、Sándor Lovas

  DOI：10.1021/jm9807151

  日期：1999.7.1

  Steric and electrostatic requirements at position 6 of [Nle(10)]NKA(4-10), a full agonist of NK-2 receptors, for molecular recognition by the receptor were studied. Two series of peptide analogues, (a) p-substituted analogues, [p-X-Phe(6),Nle(10)]NKA(4-10), where X = F, Cl, Br, I, NH2, NO2, and (b) [D-Phe(6),Nle(10)]NKA(4-10), [Trp(6),Nle(10)]NKA(4-10), and [Chex-Ala(6),Nle(10)]NKA(4-10), were synthesized, and their biological activity was examined. Competition binding experiments with [H-3]NKA were performed using cloned human NK-2 receptors expressed in CHO cells. Antagonistic and agonistic properties of the analogues were studied using an in vitro functional assay with hamster tracheal rings. The rank order of potency of agonists was [Nle(10)]NKA(4-10) approximate to [p-F-Phe(6),Nle(10)]NKA(4-10) > [p-NH2-Phe(6),Nle(10)]NKA(4-10) > [p-Cl-Phe(6),Nle(10)]NKA(4-10) > [p-NO2-Phe(6),Nle(10)]NKA(4-10) > [Trp(6),Nle(10)]NKA(4-10). Size and planarity of the aromatic side chain were crucially important for the biological activity, whereas electran-donating and electron-withdrawing properties of the para-substituent were less important;. The results favor the hypothesis that weakly polar pi-pi interactions exist between the aromatic group and the receptor.