Flu-βAla-Tyr-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Lys-Arg-NH2 | 1609495-14-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: Flu-βAla-Tyr-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Lys-Arg-NH2
• CAS: 1609495-14-8
• 化学式: C₈₈H₁₃₄N₃₂O₂₀
• 分子量: 1960.23
• InChiKey: BKJXBXZHGVOMDN-RDPZKNQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.85
• 重原子数：
  140.0
• 可旋转键数：
  63.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  919.16
• 氢给体数：
  35.0
• 氢受体数：
  28.0

反应信息

• 作为产物：
  描述：

  Fmoc-甘氨酸 、 FMOC-beta-丙氨酸 、 6-羧基荧光素 、 alkaline earth salt of/the/ methylsulfuric acid 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.9h， 以4.8 mg的产率得到Flu-βAla-Tyr-Gly-Arg-Lys-Lys-Arg-Arg-Gln-Arg-Lys-Arg-NH2
  参考文献：
  名称：

  Effect of each guanidinium group on the RNA recognition and cellular uptake of Tat-derived peptides

  摘要：

  The six arginine (Arg) residues in the human immunodeficiency virus transactivator of transcription protein (HIV Tat protein) basic region (residues 47-57) are crucial for two bioactivities: RNA recognition and cellular uptake. Herein, we report a systematic study to investigate the role of the guanidinium group on Arg at each position in Tat-derived peptides for the two bioactivities. Tat-derived peptides, in which each guanidinium-bearing arginine was replaced with a urea-bearing citrulline (Cit) or an ammonium-bearing Lys, were synthesized by solid phase peptide synthesis. RNA recognition of the peptides was studied by electrophoretic mobility shift assays, and cellular uptake into Jurkat cells was determined by flow cytometry. Our results showed that removing the positive charge and altering the hydrogen bonding capacity of Arg affect the two biological functions differently. Furthermore, the effects are position dependent. These findings should be useful for the development of functional molecules containing guanidinium, urea, and ammonium groups for RNA recognition to affect biological processes and for cellular uptake for drug delivery. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.03.037