6-aminohexyl 3β-hydroxyolean-12-en-28-oate | 1224429-27-9

• 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: 6-aminohexyl 3β-hydroxyolean-12-en-28-oate
• 英文别名: 6-aminohexyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 1224429-27-9
• 化学式: C₃₆H₆₁NO₃
• 分子量: 555.885
• InChiKey: GNYNEWDYXAOSCF-QZUHWTNASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.3
• 重原子数：
  40
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-aminohexyl 3β-hydroxyolean-12-en-28-oate 、 方酸二乙酯 以 aq. phosphate buffer 为溶剂， 反应 14.0h， 以560 mg的产率得到6-(2-ethoxy-3,4-dioxocyclobut-1-en-1-amino)hexyl 3β-hydroxyolean-12-en-28-oate
  参考文献：
  名称：

  Multivalent oleanolic acid human serum albumin conjugate as nonglycosylated neomucin for influenza virus capture and entry inhibition

  摘要：

  We report the synthesis of multivalent oleanolic acid (OA) protein conjugates as nonglycosylated neomucin mimic for the capture and entry inhibition of influenza viruses. Oleanolic acid derivatives bearing an amine-terminated linker were synthesized by esterification of carboxylic acid and further grafted onto the human serum albumin (HSA) via diethyl squarate method. The binding of hemagglutinin (HA) on the virion surface to the synthetic neomucin was evaluated by hemagglutination inhibition assay. The influenza virus capture ability of the PEGylated OA-HSA conjugate was further investigated by Dynamic Light Scattering (DLS), virus capture assay and Isothermal Titration Calorimeter (ITC) techniques. The pronounced agglutination of viral particles, the high capture efficiency and affinity constant indicate that this neoprotein is comparable to natural glycosylated mucin, suggesting that this material could potentially be used as anti-infective barriers to prevent virus from invading host cells. The study also rationalizes the feasibility of antiviral drug development based on OA or other antiviral small molecules conjugated protein strategies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.070
• 作为产物：
  描述：

  1-叠氮基-6-溴己烷 在 氢气 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 6-aminohexyl 3β-hydroxyolean-12-en-28-oate
  参考文献：
  名称：

  Multivalent oleanolic acid human serum albumin conjugate as nonglycosylated neomucin for influenza virus capture and entry inhibition

  摘要：

  We report the synthesis of multivalent oleanolic acid (OA) protein conjugates as nonglycosylated neomucin mimic for the capture and entry inhibition of influenza viruses. Oleanolic acid derivatives bearing an amine-terminated linker were synthesized by esterification of carboxylic acid and further grafted onto the human serum albumin (HSA) via diethyl squarate method. The binding of hemagglutinin (HA) on the virion surface to the synthetic neomucin was evaluated by hemagglutination inhibition assay. The influenza virus capture ability of the PEGylated OA-HSA conjugate was further investigated by Dynamic Light Scattering (DLS), virus capture assay and Isothermal Titration Calorimeter (ITC) techniques. The pronounced agglutination of viral particles, the high capture efficiency and affinity constant indicate that this neoprotein is comparable to natural glycosylated mucin, suggesting that this material could potentially be used as anti-infective barriers to prevent virus from invading host cells. The study also rationalizes the feasibility of antiviral drug development based on OA or other antiviral small molecules conjugated protein strategies. (C) 2017 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2017.10.070

文献信息

• Synthesis and Evaluation of C-28 Oleanolic Acid Derivatives as Inhibitors of Glycogen Phosphorylase
  作者：Keguang Cheng、Chao Wang、Jun Liu、Juan Xie、Hongbin Sun

  DOI：10.2174/157018010790225921

  日期：2010.2.1

  Synthesis and evaluation of C-28 oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase have been described. The results of glycogen phosphorylase inhibition assay and structure-activity relationship (SAR) analysis are also discussed.

  已经描述了作为糖原磷酸化酶的新型抑制剂的C-28齐墩果酸衍生物的合成和评价。还讨论了糖原磷酸化酶抑制试验和结构-活性关系（SAR）分析的结果。
• Multivalent oleanolic acid human serum albumin conjugate as nonglycosylated neomucin for influenza virus capture and entry inhibition
  作者：Yang Yang、Hao-Jie He、Hao Chang、Yao Yu、Mei-Bing Yang、Yun He、Zhen-Chuan Fan、Suri S. Iyer、Peng Yu

  DOI：10.1016/j.ejmech.2017.10.070

  日期：2018.1

  We report the synthesis of multivalent oleanolic acid (OA) protein conjugates as nonglycosylated neomucin mimic for the capture and entry inhibition of influenza viruses. Oleanolic acid derivatives bearing an amine-terminated linker were synthesized by esterification of carboxylic acid and further grafted onto the human serum albumin (HSA) via diethyl squarate method. The binding of hemagglutinin (HA) on the virion surface to the synthetic neomucin was evaluated by hemagglutination inhibition assay. The influenza virus capture ability of the PEGylated OA-HSA conjugate was further investigated by Dynamic Light Scattering (DLS), virus capture assay and Isothermal Titration Calorimeter (ITC) techniques. The pronounced agglutination of viral particles, the high capture efficiency and affinity constant indicate that this neoprotein is comparable to natural glycosylated mucin, suggesting that this material could potentially be used as anti-infective barriers to prevent virus from invading host cells. The study also rationalizes the feasibility of antiviral drug development based on OA or other antiviral small molecules conjugated protein strategies. (C) 2017 Elsevier Masson SAS. All rights reserved.