Leu-Val-Pro-Pro-Phe-Phe-Leu-Ile-Ile | 143796-62-7

• 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
• 英文名称: Leu-Val-Pro-Pro-Phe-Phe-Leu-Ile-Ile
• 英文别名: LVPPFFLII；H-Leu-Val-Pro-Pro-Phe-Phe-Leu-Ile-Ile-OH；(2S,3S)-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-1-[(2S)-1-[(2S)-2-[[(2S)-2-amino-4-methylpentanoyl]amino]-3-methylbutanoyl]pyrrolidine-2-carbonyl]pyrrolidine-2-carbonyl]amino]-3-phenylpropanoyl]amino]-3-phenylpropanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-3-methylpentanoic acid
• CAS: 143796-62-7
• 化学式: C₅₇H₈₇N₉O₁₀
• 分子量: 1058.37
• InChiKey: UDIRCFPDGNVYMW-PUUGUDBISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  76
• 可旋转键数：
  28
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  279
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-亮氨酸 、 (2S)-2-[(3S)-3-benzyl-4-(9H-fluoren-9-ylmethoxycarbonyl)-2-oxopiperazin-1-yl]-3-phenylpropanoic acid 、 Fmoc-L-脯氨酸 、 Fmoc-L-苯丙氨酸 、 Fmoc-L-异亮氨酸 在 哌啶 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以10 mg的产率得到Leu-Val-Pro-Pro-Phe-Phe-Leu-Ile-Ile
  参考文献：
  名称：

  Cyclolinopeptide derivatives modify methotrexate-induced suppression of the humoral immune response in mice

  摘要：

  High doses of chemotherapeutics in clinical treatment, leading to cell toxicity, can be lowered by co-administration of other immunoregulatory drugs. The aim of this study was to evaluate effects of several derivatives of cyclolinopeptide A (CLA), derived from linen seeds, on the suppressive action of metothrexate (MTX) in a mouse model of humoral immune response in vitro. New CIA analogues 1 and 2, and their linear precursors 3 and 4, containing conformationally restricted dipeptide fragment Phe-Phe or d-Phe-d-Phe with ethylene bridge (-CH2-CH2-) between phenylalanine nitrogens were synthesized. NMR studies and theoretical calculations showed that introduction of locally constraining fragment into CLA molecule increased its overall conformational flexibility.The bioactivity of new CIA analogues was examined in the mouse model of the in vitro secondary humoral immune response, suppressed by methotrexate (MTX). The results revealed differential actions of the peptides such as 1/augmentation of the suppressive activity of MIX or 2/antagonistic effects of the peptides on MIX-induced suppression. Potential advantages for the application of CIA-derived peptides in therapy and structure activity relationships were discussed. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.07.040

文献信息

• Cyclolinopeptide derivatives modify methotrexate-induced suppression of the humoral immune response in mice
  作者：Joanna Katarzyńska、Adam Mazur、Ewa Rudzińska、Jolanta Artym、Michał Zimecki、Stefan Jankowski、Janusz Zabrocki

  DOI：10.1016/j.ejmech.2011.07.040

  日期：2011.9

  High doses of chemotherapeutics in clinical treatment, leading to cell toxicity, can be lowered by co-administration of other immunoregulatory drugs. The aim of this study was to evaluate effects of several derivatives of cyclolinopeptide A (CLA), derived from linen seeds, on the suppressive action of metothrexate (MTX) in a mouse model of humoral immune response in vitro. New CIA analogues 1 and 2, and their linear precursors 3 and 4, containing conformationally restricted dipeptide fragment Phe-Phe or d-Phe-d-Phe with ethylene bridge (-CH2-CH2-) between phenylalanine nitrogens were synthesized. NMR studies and theoretical calculations showed that introduction of locally constraining fragment into CLA molecule increased its overall conformational flexibility.The bioactivity of new CIA analogues was examined in the mouse model of the in vitro secondary humoral immune response, suppressed by methotrexate (MTX). The results revealed differential actions of the peptides such as 1/augmentation of the suppressive activity of MIX or 2/antagonistic effects of the peptides on MIX-induced suppression. Potential advantages for the application of CIA-derived peptides in therapy and structure activity relationships were discussed. (C) 2011 Elsevier Masson SAS. All rights reserved.