Click-iT farnesyl alcohol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: Click-iT farnesyl alcohol
• 英文别名: Click-iT Az-F-OH；(E,E,E)-Farnesyl alcohol azide；(2E,6E,10E)-12-azido-3,7,11-trimethyldodeca-2,6,10-trien-1-ol
• 化学式: C₁₅H₂₅N₃O
• 分子量: 263.383
• InChiKey: FRARHOTUPWLCHV-RDUMTQBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  19
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  34.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  E,E,E-12-hydroxyfarnesyl acetate 在 二苯基膦叠氮化物 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 甲醇 、 potassium carbonate 作用下， 以 甲苯 为溶剂， 生成 Click-iT farnesyl alcohol 、
  参考文献：
  名称：

  Farnesyl Diphosphate Analogues with ω-Bioorthogonal Azide and Alkyne Functional Groups for Protein Farnesyl Transferase-Catalyzed Ligation Reactions

  摘要：

  [Graphics]Eleven farnesyl diphosphate analogues, which contained (omega-azide or alkyne substituents suitable for bioorthogonal Staudinger and Huisgen [3 + 2] cycloaddition coupling reactions, were synthesized. The analogues were evaluated as substrates for the alkylation of peptide cosubstrates by yeast protein farnesyl transferase. Five of the diphosphates were good alternative substrates for farnesyl diphosphate (FPP). Steady-state kinetic constants were measured for the active compounds, and the products were characterized by HPLC and LC-MS. Two of the analogues gave steady-state kinetic parameters (k(cat) and K-m) very similar to those of the natural substrate.

  DOI：

  10.1021/jo7017747