2-(trimethylsilyl)ethyl 2-deoxy-3-O-[(R)-3-decanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside | 216014-08-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: 2-(trimethylsilyl)ethyl 2-deoxy-3-O-[(R)-3-decanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6R)-3-hydroxy-2-(hydroxymethyl)-5-(2,2,2-trichloroethoxycarbonylamino)-6-(2-trimethylsilylethoxy)oxan-4-yl] (3R)-3-decanoyloxytetradecanoate
• CAS: 216014-08-3
• 化学式: C₃₈H₇₀Cl₃NO₁₀Si
• 分子量: 835.419
• InChiKey: GBQKYXIEGWXWEB-XBDYLYHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.16
• 重原子数：
  53
• 可旋转键数：
  32
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  150
• 氢给体数：
  3
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2-deoxy-3-O-[(R)-3-decanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 吡啶 、 2-(吡咯烷-1-基)吡啶 、 1,1-二氯甲醚 、 N,N-二异丙基乙胺 、 zinc(II) chloride 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 8.5h， 生成 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-decanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl chloride
  参考文献：
  名称：

  3-O-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities

  摘要：

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.

  DOI：

  10.1021/jm990222b
• 作为产物：
  描述：

  (R)-3-decanoyloxytetradecanoic acid 在 EDC.MeI 、 4-吡咯烷基吡啶 作用下， 以 aqueous AcOH 、 二氯甲烷 为溶剂， 以1.30 g (77%)的产率得到2-(trimethylsilyl)ethyl 2-deoxy-3-O-[(R)-3-decanoyloxytetradecanoyl]-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Aminoalkyl glucosamine phosphate compounds and their use as adjuvants

  摘要：

  描述并声明了一种氨基糖氨磷酸化合物，用作辅助剂和免疫效应物质。这些化合物在糖苷键中含有2-脱氧-2-氨基葡萄糖与氨基烷基（缺糖原）基团。这些化合物在葡萄糖胺环上的第4或第6碳上磷酸化，并包括三个3-烷酰氧烷酰残基。这些化合物增强了免疫动物中的抗体产生，同时刺激细胞因子的产生并激活巨噬细胞。还公开了使用这些化合物作为辅助剂和免疫效应物质的方法。

  公开号：

  US06113918A1

文献信息

• Aminoalkyl glucosamine phosphate compounds and their use as adjuvants
  申请人：Ribi ImmunoChem Research, Inc.

  公开号：US06113918A1

  公开（公告）日：2000-09-05

  Aminoalkyl glucosamine phosphate compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosamine ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

  描述并声明了一种氨基糖氨磷酸化合物，用作辅助剂和免疫效应物质。这些化合物在糖苷键中含有2-脱氧-2-氨基葡萄糖与氨基烷基（缺糖原）基团。这些化合物在葡萄糖胺环上的第4或第6碳上磷酸化，并包括三个3-烷酰氧烷酰残基。这些化合物增强了免疫动物中的抗体产生，同时刺激细胞因子的产生并激活巨噬细胞。还公开了使用这些化合物作为辅助剂和免疫效应物质的方法。
• Aminoalkyl glucosaminide phosphate compounds and their use as adjuvants and immunoeffectors
  申请人：Corixa Corporation

  公开号：US06303347B1

  公开（公告）日：2001-10-16

  Aminoalkyl glucosaminide phosphate (AGP) compounds that are adjuvants and immunoeffectors are described and claimed. The compounds have a 2-deoxy-2-amino glucose in glycosidic linkage with an aminoalkyl (aglycon) group. Compounds are phosphorylated at the 4 or 6 carbon on the glucosaminide ring and comprise three 3-alkanoyloxyalkanoyl residues. The compounds augment antibody production in immunized animals as well as stimulate cytokine production and activate macrophages. Methods for using the compounds as adjuvants and immunoeffectors are also disclosed.

  描述和声明了一种作为辅助剂和免疫效应物的氨基糖胺磷酸酯（AGP）化合物。这些化合物具有一个2-脱氧-2-氨基葡萄糖与氨基烷基（糖苷）基团的糖苷键连接。这些化合物在葡萄糖氨基糖环的4或6碳上磷酸化，并包含三个3-烷酰氧烷酰残基。这些化合物增强了免疫动物中的抗体产生，同时刺激细胞因子的产生并激活巨噬细胞。还公开了将这些化合物用作辅助剂和免疫效应物的方法。
• 3-<i>O</i>-Desacyl Monophosphoryl Lipid A Derivatives:  Synthesis and Immunostimulant Activities
  作者：David A. Johnson、David S. Keegan、C. Gregory Sowell、Mark T. Livesay、Craig L. Johnson、Lara M. Taubner、Annalivia Harris、Kent R. Myers、Jennifer D. Thompson、Gary L. Gustafson、Michael J. Rhodes、J. Terry Ulrich、Jon R. Ward、Yvonne M. Yorgensen、John L. Cantrell、Valerie G. Brookshire

  DOI：10.1021/jm990222b

  日期：1999.11.1

  The synthesis of a series of novel analogues of lipid A, the active principle of lipopolysaccharide, is reported. In these compounds, the 1-O-phosphono and (R)-3-hydroxytetradecanoyl moieties of native Salmonella minnesota R595 lipid A have been replaced with hydrogen and the length of the normal fatty acyl residues has been systematically varied. Normal fatty acid chain length in the 3-O-desacyl monophosphoryl lipid A (MLS) series is shown to be a critical determinant of iNOS gene expression in activated mouse macrophages and the induction of proinflammatory cytokines in human peripheral monocytes. Examination of pyrogenicity in rabbits and lethal toxicity in D-galactosamine-treated mice shows that toxic effects in the MLA series can be ameliorated by modifying fatty acid chain length. When used as an adjuvant for tetanus toroid vaccines, certain MLA derivatives enhance the production of tetanus toroid-specific antibodies in mice.