(+)-biotinyl-4,7,10,13,16-pentaoxa-1,19-diaminononadecane | 869354-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: (+)-biotinyl-4,7,10,13,16-pentaoxa-1,19-diaminononadecane
• 英文别名: N-(19-Amino-4,7,10,13,16-pentaoxanonadecyl)-5-((3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanamide；5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[3-[2-[2-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]ethoxy]ethoxy]propyl]pentanamide
• CAS: 869354-65-4
• 化学式: C₂₄H₄₆N₄O₇S
• 分子量: 534.718
• InChiKey: AAPRTYNXINRWDQ-FUDKSRODSA-N

物化性质

• 沸点：
  756.3±60.0 °C(Predicted)
• 密度：
  1.136±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  36
• 可旋转键数：
  24
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  168
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  azidoacetic anhydride 、 (+)-biotinyl-4,7,10,13,16-pentaoxa-1,19-diaminononadecane 在 吡啶 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以61%的产率得到
  参考文献：
  名称：

  Convenient Synthesis of a Propargylated Cyclic (3′-5′) Diguanylic Acid and Its “Click” Conjugation to a Biotinylated Azide

  摘要：

  The ribonucleoside building block, N(2)-isobutyryl-2'-O-propargyl-3'-O-levulinyl guanosine, was prepared from commercial N(2)-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-propargyl guanosine in a yield of 91%. The propargylated guanylyl(3'-5')guanosine phosphotriester was synthesized from the reaction of N(2)-isobutyryl-2'-O-propargyl-3'-O-levulinyl guanosine with N(2)-isobutyryl-5'-O-(4,4'-dimethoxytrityl)-2'-O-tert-butyldimethylsilyl-3'-O-[(2-cyanoethyl)-N, N-diisopropylaminophosphinyl] guanosine and isolated in a yield of 88% after P(III) oxidation, 3'-/5'-deprotection, and purification. The propargylated guanylyl(3'-5')guanosine phosphotriester was phosphitylated using 2-cyanoethyl tetraisopropylphosphordiamidite and 1H-tetrazole and was followed by an in situ intramolecular cyclization to give a propargylated c-di-GMP triester, which was isolated in a yield of 40% after P(III) oxidation and purification. Complete N-deacylation of the guanine bases and removal of the 2-cyanoethyl phosphate protecting groups from the propargylated c-di-GMP triester were performed by treatment with aqueous ammonia at ambient temperature. The final 2'-desilylation reaction was effected by exposure to triethylammonium trihydrofluoride affording the desired propargylated c-di-GMP diester, the purity of which exceeded 95%. Biotinylation of the propargylated c-di-GMP diester was easily accomplished through its cycloaddition reaction with a biotinylated azide derivative under click conditions to produce the biotinylated c-di-GMP conjugate of interest in an isolated yield of 62%.

  DOI：

  10.1021/bc1003857