62-acetoxy-4,8,12,16,20,24,28,32,36,40,44,48,52,56,60-pentadecamethyldohexaconta-4E,8E,12Z,16Z,20Z,24Z,28Z,32Z,36Z,40Z,44Z,48Z,52Z,56Z-tetradecaenal | 369594-11-6

• 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: 62-acetoxy-4,8,12,16,20,24,28,32,36,40,44,48,52,56,60-pentadecamethyldohexaconta-4E,8E,12Z,16Z,20Z,24Z,28Z,32Z,36Z,40Z,44Z,48Z,52Z,56Z-tetradecaenal
• CAS: 369594-11-6
• 化学式: C₇₉H₁₂₈O₃
• 分子量: 1125.88
• InChiKey: DZAUIADWZJGBRY-HHZZJVLISA-N

反应信息

• 作为反应物：
  描述：

  62-acetoxy-4,8,12,16,20,24,28,32,36,40,44,48,52,56,60-pentadecamethyldohexaconta-4E,8E,12Z,16Z,20Z,24Z,28Z,32Z,36Z,40Z,44Z,48Z,52Z,56Z-tetradecaenal 在 3 A molecular sieve 、 potassium carbonate 、 四丁基磷酸氢铵 、 三氯乙腈 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 26.58h， 生成 3,7,11,15,19,23,27,31,35,39,43,47,51,55,59-pentadecamethyl-62-(1-naphthyl)aminodohexaconta-6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,50Z,54E,58E-tetradecaenyl phosphate diammonium salt
  参考文献：
  名称：

  摘要：

  A series of fluorescent dolichyl phosphates containing the (1-naphthyl)amino group in the omega-fragment of the chain and possessing a definite distance between fluorophoric and phosphate groups were synthesized for studying the interactions of dolichyl phosphates with enzymes and biological membranes. The corresponding terminal 2,3-dihydrohexadeca-, 2,3-dihydroundeca-, and 2,3-dihydrooctaprenol epoxides were obtained from racemic dolichols (prepared from natural polyprenol mixtures) by van Tamelen epoxidation of their omega-isoprene unit and separated by preparative HPLC. These epoxides were converted to aldehydes, which were subjected to reductive amination with 1-aminonaphthalene and NaBH4 with subsequent phosphorylation of the resulting amino alcohols.

  DOI：

  10.1023/a:1015034309170
• 作为产物：
  描述：

  3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63-hexadecamethyl-62,63-epoxytetrahexaconta-6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54E,58E-tetradecaen-1-yl acetate 在 过碘酸 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 0.42h， 以85%的产率得到62-acetoxy-4,8,12,16,20,24,28,32,36,40,44,48,52,56,60-pentadecamethyldohexaconta-4E,8E,12Z,16Z,20Z,24Z,28Z,32Z,36Z,40Z,44Z,48Z,52Z,56Z-tetradecaenal
  参考文献：
  名称：

  摘要：

  A series of fluorescent dolichyl phosphates containing the (1-naphthyl)amino group in the omega-fragment of the chain and possessing a definite distance between fluorophoric and phosphate groups were synthesized for studying the interactions of dolichyl phosphates with enzymes and biological membranes. The corresponding terminal 2,3-dihydrohexadeca-, 2,3-dihydroundeca-, and 2,3-dihydrooctaprenol epoxides were obtained from racemic dolichols (prepared from natural polyprenol mixtures) by van Tamelen epoxidation of their omega-isoprene unit and separated by preparative HPLC. These epoxides were converted to aldehydes, which were subjected to reductive amination with 1-aminonaphthalene and NaBH4 with subsequent phosphorylation of the resulting amino alcohols.

  DOI：

  10.1023/a:1015034309170

文献信息

• Synthesis of dolichyl phosphate derivatives with fluorescent label at the ω-end of the chain, new tools to study protein glycosylation
  作者：Vladimir N Shibaev、Vladimir V Veselovsky、Antonina V Lozanova、Sergei D Maltsev、Leonid L Danilov、W.Thomas Forsee、Jun Xing、Herbert C Cheung、Mark J Jedrzejas

  DOI：10.1016/s0960-894x(99)00662-9

  日期：2000.1

  Derivatives of dolichyl phosphate (Dol-P) with 2-aminopyridine or 1-aminonaphtalene fluorophore groups at the omega-end of the chain were synthesized. These products serve as substrates for recombinant yeast Dol-P-mannose synthase. Fluorescence resonance energy transfer between a Trp residue of the enzyme and the 1-aminonaphtalene group of the Dol-P analogue was demonstrated. (C) 2000 Elsevier Science Ltd. All rights reserved.