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,46Z,50Z,54E,58E-tetradecaen-1-ol | 444765-76-8

• 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: 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,46Z,50Z,54E,58E-tetradecaen-1-ol
• CAS: 444765-76-8
• 化学式: C₈₇H₁₃₅NO
• 分子量: 1211.03
• InChiKey: SOXMVYJNSGVVNA-FXIXEUGRSA-N

反应信息

• 作为反应物：
  描述：

  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,46Z,50Z,54E,58E-tetradecaen-1-ol 在 四丁基磷酸氢铵 、 三氯乙腈 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 生成 [(6Z,10Z,14Z,18Z,22Z,26Z,30Z,34Z,38Z,42Z,46Z,50Z,54E,58E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59-pentadecamethyl-62-(naphthalen-1-ylamino)dohexaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58-tetradecaenyl] dihydrogen phosphate
  参考文献：
  名称：

  Synthesis of dolichyl phosphate derivatives with fluorescent label at the ω-end of the chain, new tools to study protein glycosylation

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00662-9
• 作为产物：
  描述：

  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,46Z,50Z,54E,58E-tetradecaen-1-yl acetate 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 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,46Z,50Z,54E,58E-tetradecaen-1-ol
  参考文献：
  名称：

  Synthesis of dolichyl phosphate derivatives with fluorescent label at the ω-end of the chain, new tools to study protein glycosylation

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(99)00662-9

文献信息

• ——
  作者：V. V. Veselovsky、A. V. Lozanova、S. D. Maltsev、L. L. Danilov、V. N. Shibaev、M. J. Jedrzejas

  DOI：10.1023/a:1015034309170

  日期：——

  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.