8-(4-benzoylbenzoyloxy)-geraniol | 183376-17-2

• 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-(4-benzoylbenzoyloxy)-geraniol
• 英文别名: [(2E,6E)-8-hydroxy-2,6-dimethylocta-2,6-dienyl] 4-benzoylbenzoate
• CAS: 183376-17-2
• 化学式: C₂₄H₂₆O₄
• 分子量: 378.468
• InChiKey: GVJZQKZHWIAIJF-OCBACMADSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-(4-benzoylbenzoyloxy)-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-(4-benzoylbenzoyloxy)-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：

  4-苯甲酰基苯甲酰氯 在 ammonium hydroxide 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 7.0h， 生成 8-(4-benzoylbenzoyloxy)-geraniol
  参考文献：
  名称：

  含苯甲酰基苯甲酸酯的焦磷酸法呢基酯的光活性类似物：酵母蛋白法呢基转移酶的合成及其在光亲和标记中的应用。

  摘要：

  法呢基焦磷酸酯（FPP）参与了许多细胞过程，包括与癌症相关的Ras蛋白转化突变体的异戊二烯化。光敏类似物可以提供有关结合法呢基焦磷酸的酶活性位点的有用信息；但是，这类化合物的可用性极为有限。结合二苯甲酮部分的分子是有吸引力的光亲和标记试剂，因为它们有用的光化学性质。在此，描述了含有对位和间位取代的苯甲酰基苯甲酸酯的两种化合物3a和3b的合成。化合物3a和3b是酵母蛋白法呢基转移酶（PFTase）的竞争性抑制剂（相对于FPP），K（i）值分别为910和380 nM。两种化合物均会在光解后使PFTase失活，导致多达44％的酶活性失活。在[（32）P] 3a或[（32）P] 3b存在的情况下，PFTase的光解作用会导致β亚基的优先标记，表明该亚基参与异戊二烯基识别。这些化合物应该是研究以FPP为底物的酶的有价值的工具。

  DOI：

  10.1021/jo9602736

文献信息

• Synthesis and rapid purification of 32P-labeled photoactive analogs of farnesyl pyrophosphate
  作者：Tammy C. Turek、Igor Gaon、Mark D. Distefano

  DOI：10.1002/(sici)1099-1344(199702)39:2<139::aid-jlcr951>3.0.co;2-a

  日期：1997.2

  Ci/mol specific activity. Further purification by preparative thin layer chromatography yielded material with a radiochemical purity of 90%. A second analog, [32P]-3b, was prepared from 1.2 mg of alcohol 4b and was obtained in 1.0% yield, 54% radiochemical purity and 700 Ci/mol specific activity. Further purification by preparative thin layer chromatography yielded material with a radiochemical purity of

  为了研究蛋白质异戊二烯转移酶的结合位点，我们合成了含有光活性二苯甲酮单元的光亲和标记类似物。在这里，我们描述了两种 32P 标记类似物的合成和快速纯化方法；通过将相应的醇与 CCl3CN 和 [32P]-H3PO4 在 CH3CN 中反应来完成磷酸化，并使用 C18 反相小柱进行纯化。类似物[32P]-3a由2.4mg起始醇4a制备并以3.3%的产率、50%的放射化学纯度和480Ci/mol的比活性获得。通过制备型薄层色谱进一步纯化得到放射化学纯度为 90% 的材料。第二种类似物[32P]-3b由1.2mg醇4b制备并以1.0％产率、54％放射化学纯度和700Ci/mol比活性获得。通过制备型薄层色谱进一步纯化得到放射化学纯度为 91% 的材料。© 1997 约翰威利父子公司。
• 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.
• Photoactive Analogs of Farnesyl Pyrophosphate Containing Benzoylbenzoate Esters:  Synthesis and Application to Photoaffinity Labeling of Yeast Protein Farnesyltransferase
  作者：Igor Gaon、Tammy C. Turek、Valerie A. Weller、Rebecca L. Edelstein、Satinder K. Singh、Mark D. Distefano

  DOI：10.1021/jo9602736

  日期：1996.1.1

  Farnesyl pyrophosphate (FPP) is involved in a large number of cellular processes including the prenylation of transforming mutants of Ras proteins implicated in cancer. Photoactive analogs could provide useful information about enzyme active sites that bind farnesyl pyrophosphate; however, the availability of such compounds is extremely limited. Molecules that incorporate benzophenone moieties are

  法呢基焦磷酸酯（FPP）参与了许多细胞过程，包括与癌症相关的Ras蛋白转化突变体的异戊二烯化。光敏类似物可以提供有关结合法呢基焦磷酸的酶活性位点的有用信息；但是，这类化合物的可用性极为有限。结合二苯甲酮部分的分子是有吸引力的光亲和标记试剂，因为它们有用的光化学性质。在此，描述了含有对位和间位取代的苯甲酰基苯甲酸酯的两种化合物3a和3b的合成。化合物3a和3b是酵母蛋白法呢基转移酶（PFTase）的竞争性抑制剂（相对于FPP），K（i）值分别为910和380 nM。两种化合物均会在光解后使PFTase失活，导致多达44％的酶活性失活。在[（32）P] 3a或[（32）P] 3b存在的情况下，PFTase的光解作用会导致β亚基的优先标记，表明该亚基参与异戊二烯基识别。这些化合物应该是研究以FPP为底物的酶的有价值的工具。