(5E,9E,13E,17E)-5,9,14,18,22-pentamethyltricosa-5,9,13,17,21-pentaen-2-one | 138181-63-2

• 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: (5E,9E,13E,17E)-5,9,14,18,22-pentamethyltricosa-5,9,13,17,21-pentaen-2-one
• CAS: 138181-63-2
• 化学式: C₂₈H₄₆O
• 分子量: 398.673
• InChiKey: DUWKADCNMMCERA-OGDZRKEVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  29
• 可旋转键数：
  15
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  methylenedimethyl sulfurane 、 (5E,9E,13E,17E)-5,9,14,18,22-pentamethyltricosa-5,9,13,17,21-pentaen-2-one 以 四氢呋喃 为溶剂， 以2 mg的产率得到
  参考文献：
  名称：

  纯重组体的制备方法。使用杆状病毒表达系统的酿酒酵母羊毛甾醇合酶。环氧乙烷裂解和 A 环形成在 2,3-氧化角鲨烯生物合成羊毛甾醇中协同作用的证据

  摘要：

  羊毛甾醇合酶 [(S)-2,3-环氧角鲨烯变位酶（环化，羊毛甾醇形成），EC 5.4.99.7]，来自酿酒酵母的酶，催化甾醇生物合成中复杂的环化/重排步骤，在杆状病毒感染的细胞中过表达并分三步纯化至均一。使用纯酶，使用 Michaelis-Menten 分析对 2,3-氧化角鲨烯 (1) 和其中 C-6 甲基被 H (3) 或 Cl (4) 替代的两种类似物进行环化动力学测定。测得的 1、3 和 4 的 Vmax/KM 比值分别为 138、9.4 和 21.9，这清楚地表明环氧乙烷裂解和环化形成 A 环是一致的，因为最接近的双环的亲核性键影响环氧乙烷裂解的速率。通过原子吸收分析，在纯化的羊毛甾醇合酶中没有检测到催化金属离子。六个高度保守的天冬氨酸残基（D → N 突变）中的每一个的定点诱变研究和...

  DOI：

  10.1021/ja963227w
• 作为产物：
  描述：

  (4E,8E,12E,16E)-4,8,13,17,21-pentamethyldocosa-4,8,12,16,20-pentaenal 在 pyridiniumchlorochromate on aluminumoxide 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 28.0h， 生成 (5E,9E,13E,17E)-5,9,14,18,22-pentamethyltricosa-5,9,13,17,21-pentaen-2-one
  参考文献：
  名称：

  纯重组体的制备方法。使用杆状病毒表达系统的酿酒酵母羊毛甾醇合酶。环氧乙烷裂解和 A 环形成在 2,3-氧化角鲨烯生物合成羊毛甾醇中协同作用的证据

  摘要：

  羊毛甾醇合酶 [(S)-2,3-环氧角鲨烯变位酶（环化，羊毛甾醇形成），EC 5.4.99.7]，来自酿酒酵母的酶，催化甾醇生物合成中复杂的环化/重排步骤，在杆状病毒感染的细胞中过表达并分三步纯化至均一。使用纯酶，使用 Michaelis-Menten 分析对 2,3-氧化角鲨烯 (1) 和其中 C-6 甲基被 H (3) 或 Cl (4) 替代的两种类似物进行环化动力学测定。测得的 1、3 和 4 的 Vmax/KM 比值分别为 138、9.4 和 21.9，这清楚地表明环氧乙烷裂解和环化形成 A 环是一致的，因为最接近的双环的亲核性键影响环氧乙烷裂解的速率。通过原子吸收分析，在纯化的羊毛甾醇合酶中没有检测到催化金属离子。六个高度保守的天冬氨酸残基（D → N 突变）中的每一个的定点诱变研究和...

  DOI：

  10.1021/ja963227w

文献信息

• Oligonucleotides, compositions and methods thereof
  申请人：WAVE LIFE SCIENCES LTD.

  公开号：US11013757B2

  公开（公告）日：2021-05-25

  The present disclosure pertains to the recognition that immune responses mediated by CpG oligonucleotides can be affected by the stereochemistry of modified internucleotidic linkages such as phosphorothioates. In some embodiments, the present disclosure relates to chirally controlled CpG oligonucleotide compositions comprising CpG oligonucleotides comprising multiple modified internucleotidic linkages such as phosphorothioate linkages, wherein the oligonucleotides comprise one or more CpG region motifs having defined stereochemistry patterns of chiral internucleotidic linkages. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are capable of agonizing an immune response. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are antagonistic. Methods for making and using chirally controlled CpG oligonucleotide compositions are also described. In some embodiments, no immune modulation is desired, and the present disclosure provides methods of identifying chirally controlled oligonucleotide compositions which have decreased immune modulation.

  本公开涉及这样一种认识，即 CpG 寡核苷酸介导的免疫反应可受硫代磷酸酯等修饰的核苷酸间连接的立体化学的影响。在一些实施方案中，本公开涉及手性控制的 CpG 寡核苷酸组合物，该组合物包含CpG 寡核苷酸，该CpG 寡核苷酸包含多个修饰的核苷酸间连接，如硫代磷酸酯连接，其中寡核苷酸包含一个或多个 CpG 区域基序，该 CpG 区域基序具有手性核苷酸间连接的确定立体化学模式。在一些实施方案中，包含一个或多个 CpG 区域基团的 CpG 寡核苷酸能够激动免疫反应。在某些实施方案中，包含一个或多个 CpG 区域基团的 CpG 寡核苷酸具有拮抗作用。还描述了制作和使用啁啾控制 CpG 寡核苷酸组合物的方法。在某些实施方案中，不需要免疫调节，本公开提供了确定免疫调节性降低的手性控制寡核苷酸组合物的方法。
• Terminal difluoro olefin analogs of squalene are time-dependent inhibitors of squalene epoxidase
  作者：William R. Moore、Gerald L. Schatzman、Esa T. Jarvi、Raymond S. Gross、James R. McCarthy

  DOI：10.1021/ja00027a056

  日期：1992.1
• OLIGONUCLEOTIDES, COMPOSITIONS AND METHODS THEREOF
  申请人：WAVE LIFE SCIENCES LTD.

  公开号：US20190209604A1

  公开（公告）日：2019-07-11

  The present disclosure pertains to the recognition that immune responses mediated by CpG oligonucleotides can be affected by the stereochemistry of modified internucleotidic linkages such as phosphorothioates. In some embodiments, the present disclosure relates to chirally controlled CpG oligonucleotide compositions comprising CpG oligonucleotides comprising multiple modified internucleotidic linkages such as phosphorothioate linkages, wherein the oligonucleotides comprise one or more CpG region motifs having defined stereochemistry patterns of chiral internucleotidic linkages. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are capable of agonizing an immune response. In some embodiments, CpG oligonucleotides comprising one or more CpG region motifs are antagonistic. Methods for making and using chirally controlled CpG oligonucleotide compositions are also described. In some embodiments, no immune modulation is desired, and the present disclosure provides methods of identifying chirally controlled oligonucleotide compositions which have decreased immune modulation.
• [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET PROCÉDÉS ASSOCIÉS
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2017062862A2

  公开（公告）日：2017-04-13

  Among other things, the present disclosure relates to designed oligonucleotides, compositions, and methods thereof. In some embodiments, provided oligonucleotide compositions provide altered splicing of a transcript. In some embodiments, provided oligonucleotide compositions have low toxicity. In some embodiments, provided oligonucleotide compositions provide improved protein binding profiles. In some embodiments, provided oligonucleotide compositions have improved delivery. In some embodiments, provided oligonucleotide compositions have improved uptake. In some embodiments, the present disclosure provides methods for treatment of diseases using provided oligonucleotide compositions.
• [EN] OLIGONUCLEOTIDE COMPOSITIONS AND METHODS THEREOF<br/>[FR] COMPOSITIONS D'OLIGONUCLÉOTIDES ET MÉTHODES ASSOCIÉES
  申请人：WAVE LIFE SCIENCES LTD

  公开号：WO2018067973A1

  公开（公告）日：2018-04-12

  Among other things, the present disclosure relates to designed oligonucleotides, compositions, and methods thereof. In some embodiments, provided oligonucleotide compositions provide altered splicing of a transcript. In some embodiments, provided oligonucleotide compositions have low toxicity. In some embodiments, provided oligonucleotide compositions provide improved protein binding profiles. In some embodiments, provided oligonucleotide compositions have improved delivery. In some embodiments, provided oligonucleotide compositions have improved uptake. In some embodiments, the present disclosure provides methods for treatment of diseases using provided oligonucleotide compositions.