Ac-U-N-I-I-U-P-L-L-U-P-I-C | 1058648-78-4

• 分子结构分类: 有机化合物 - 有机聚合物 - 多肽
• 英文名称: Ac-U-N-I-I-U-P-L-L-U-P-I-C
• CAS: 1058648-78-4
• 化学式: C₆₁H₁₀₅N₁₃O₁₅S
• 分子量: 1292.65
• InChiKey: JJWRQLPRJQBVSZ-DNZPMXJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  90.0
• 可旋转键数：
  35.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  412.01
• 氢给体数：
  13.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  二乙酰荧光素-5-马来亚胺 、 Ac-U-N-I-I-U-P-L-L-U-P-I-C 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以60%的产率得到
  参考文献：
  名称：

  Translocation of an Aib-containing peptide through cell membranes

  摘要：

  The biophysical characteristics and channel-forming activity of peptaibols inserted into artificial membranes have been studied over the last 30 years. However, to our knowledge, no studies have addressed directly their behavior in living cells. In this work, a novel strategy has been employed to precisely assess the living cell membrane-penetrating activity of a fluorescein-labeled Aib (alpha-aminoisobutyric acid)-containing peptide derived from a peptaibol, trichorovin-XIIa (TV-XIIa). We have demonstrated for the first time that the peptide containing an unusual amino acid residue, Aib, is taken up by cells via a non endocytic pathway. The replacement of Aib in the TV-XIIa sequence with Ala inhibits the cellular uptake. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.005
• 作为产物：
  描述：

  Rink amide resin 、 9H-fluoren-9-ylmethyl N-[(2S)-4-amino-1-fluoro-1,4-dioxobutan-2-yl]carbamate 、 Fmoc-L-亮氨酸 、 Fmoc-L-脯氨酸 、 乙酸酐 、 Fmoc-L-异亮氨酸 、 Fmoc-Ile-F 、 芴甲氧羰基-L-半胱氨酸 、 Fmoc-Aib-F 在 1-羟基苯并三唑 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.33h， 生成 Ac-U-N-I-I-U-P-L-L-U-P-I-C
  参考文献：
  名称：

  Translocation of an Aib-containing peptide through cell membranes

  摘要：

  The biophysical characteristics and channel-forming activity of peptaibols inserted into artificial membranes have been studied over the last 30 years. However, to our knowledge, no studies have addressed directly their behavior in living cells. In this work, a novel strategy has been employed to precisely assess the living cell membrane-penetrating activity of a fluorescein-labeled Aib (alpha-aminoisobutyric acid)-containing peptide derived from a peptaibol, trichorovin-XIIa (TV-XIIa). We have demonstrated for the first time that the peptide containing an unusual amino acid residue, Aib, is taken up by cells via a non endocytic pathway. The replacement of Aib in the TV-XIIa sequence with Ala inhibits the cellular uptake. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.06.005