8-(3-benzoylphenyloxy)-geraniol | 196312-03-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 8-(3-benzoylphenyloxy)-geraniol
• 英文别名: [3-[(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienoxy]phenyl]-phenylmethanone
• CAS: 196312-03-5
• 化学式: C₂₃H₂₆O₃
• 分子量: 350.458
• InChiKey: ARFWWAZCDHUGIH-KKEAHIQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  8-(3-benzoylphenyloxy)-geraniol 在 N-氯代丁二酰亚胺 、 二甲基硫 、 氨 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 S-[8-(3-benzoylphenyloxy)-geranyl]-cysteine methyl ester
  参考文献：
  名称：

  Synthesis and Biological Activity of Photoactivatable N-Ras Peptides and Proteins

  摘要：

  A modular strategy for the assembly of farnesylated N-Ras heptapeptides carrying a photo-activatable benzophenone (BP) group within the lipid residue is described. This strategy is based on the fragment condensation of a N-terminal hexapeptide synthesized on the solid support with a cysteine methyl ester which is modified with different farnesyl analogues, incorporating the photophor. At the N-terminus of the peptides different functional groups can be attached, e.g., biotin for product enrichment and detection after photoactivation or a maleimido (MIC) linker, allowing for the coupling to proteins carrying a C-terminal free cysteine. Using this strategy, 24 peptides were synthesized, incorporating famesyl analogues with four different chain lengths. Two of these photoactivatable conjugates were ligated to oncogenic human N-RasG12VDelta181. A cellular transformation assay revealed that the semisynthetic proteins retain their biological activity despite the photolabel. The first photolabeling experiments with a geranyl-BP-labeled N-Ras construct and the farnesyl-sensitive guanine nucleotide exchange factor hSos1 indicate that this photoaffinity labeling system can be particularly useful for studying protein-protein interactions, e.g., the participation of the farnesyl group in Ras signaling, which is still discussed with controversy.

  DOI：

  10.1021/ja036178d
• 作为产物：
  描述：

  {3-[(2E,6E)-8-(tert-Butyl-dimethyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienyloxy]-phenyl}-phenyl-methanone 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以97%的产率得到8-(3-benzoylphenyloxy)-geraniol
  参考文献：
  名称：

  Benzoylphenoxy analogs of isoprenoid diphosphates as photoactivatable substrates for bacterial prenyltransferases

  摘要：

  Photoactivatable benzophenone-containing analogs of isoprenyl diphosphates have been synthesized and evaluated as substrates and inhibitors of three bacterial prenyltransferases: farnesyl diphosphate synthase (FPS), hexaprenyl diphosphate synthase (HexPS)and undecaprenyl diphosphate synthase (UPS). These analogs undergo chain extension and will allow identification of hydrophobic active site residues of these enzymes. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00342-9

文献信息

• Synthesis and Biological Activity of Photoactivatable <i>N</i>-Ras Peptides and Proteins
  作者：Martin Völkert、Koji Uwai、Andreas Tebbe、Boriana Popkirova、Melanie Wagner、Jürgen Kuhlmann、Herbert Waldmann

  DOI：10.1021/ja036178d

  日期：2003.10.1

  A modular strategy for the assembly of farnesylated N-Ras heptapeptides carrying a photo-activatable benzophenone (BP) group within the lipid residue is described. This strategy is based on the fragment condensation of a N-terminal hexapeptide synthesized on the solid support with a cysteine methyl ester which is modified with different farnesyl analogues, incorporating the photophor. At the N-terminus of the peptides different functional groups can be attached, e.g., biotin for product enrichment and detection after photoactivation or a maleimido (MIC) linker, allowing for the coupling to proteins carrying a C-terminal free cysteine. Using this strategy, 24 peptides were synthesized, incorporating famesyl analogues with four different chain lengths. Two of these photoactivatable conjugates were ligated to oncogenic human N-RasG12VDelta181. A cellular transformation assay revealed that the semisynthetic proteins retain their biological activity despite the photolabel. The first photolabeling experiments with a geranyl-BP-labeled N-Ras construct and the farnesyl-sensitive guanine nucleotide exchange factor hSos1 indicate that this photoaffinity labeling system can be particularly useful for studying protein-protein interactions, e.g., the participation of the farnesyl group in Ras signaling, which is still discussed with controversy.
• Benzoylphenoxy analogs of isoprenoid diphosphates as photoactivatable substrates for bacterial prenyltransferases
  作者：Dale M. Marecak、Yutaka Horiuchi、Hiroyuki Arai、Masahiro Shimonaga、Yuji Maki、Tanetoshi Koyama、Kyozo Ogura、Glenn D. Prestwich

  DOI：10.1016/s0960-894x(97)00342-9

  日期：1997.8

  Photoactivatable benzophenone-containing analogs of isoprenyl diphosphates have been synthesized and evaluated as substrates and inhibitors of three bacterial prenyltransferases: farnesyl diphosphate synthase (FPS), hexaprenyl diphosphate synthase (HexPS)and undecaprenyl diphosphate synthase (UPS). These analogs undergo chain extension and will allow identification of hydrophobic active site residues of these enzymes. (C) 1997 Elsevier Science Ltd.