N-[(R)-3-decanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-decanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serinamide | 216014-84-5

• 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: N-[(R)-3-decanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-decanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serinamide
• 英文别名: [(2R,3R,4R,5S,6R)-2-[(2S)-3-amino-2-[[(3R)-3-decanoyloxytetradecanoyl]amino]-3-oxopropoxy]-5-diphenoxyphosphoryloxy-3-(2,2,2-trichloroethoxycarbonylamino)-6-[(1,1,1-trichloro-2-methylpropan-2-yl)oxycarbonyloxymethyl]oxan-4-yl] (3R)-3-decanoyloxytetradecanoate
• CAS: 216014-84-5
• 化学式: C₇₇H₁₂₂Cl₆N₃O₁₉P
• 分子量: 1637.52
• InChiKey: DQYQEUGUUDJGSR-KSIVTWNPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  24.7
• 重原子数：
  106
• 可旋转键数：
  65
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  288
• 氢给体数：
  3
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  N-[(R)-3-decanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-decanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serinamide 在 溶剂黄146 、 锌 作用下， 生成
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of vaccine adjuvants: aminoalkyl glucosaminide 4-phosphates (AGPs)

  摘要：

  A novel series of acylated omega-aminoalkyl 2-amino-2-deoxy-4-phosphono-beta-D-glucopyranosides (aminoalkyl glucosaminide 4-phosphates) was synthesized and screened for immunostimulant activity. Several of these compounds enhance the production of tetanus toroid-specific antibodies in mice and augment vaccine-induced cytotoxic T cells against EG.7-ova target cells. (C) 1999 Elsevier Science Ltd. Pill rights reserved.

  DOI：

  10.1016/s0960-894x(99)00374-1
• 作为产物：
  描述：

  N-[(R)-3-decanoyloxytetradecanoyl]-L-serinamide 、 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 在 silver trifluoromethanesulfonate 作用下， 以56%的产率得到N-[(R)-3-decanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-decanoyloxytetradecanoyl]-6-O-(2,2,2-trichloro-1,1-dimethylethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-serinamide
  参考文献：
  名称：

  Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors

  摘要：

  描述和声明了一种氨基糖胺磷酸盐化合物，它们是辅助剂和免疫效应物质。这些化合物具有一个2-脱氧-2-氨基葡萄糖与一个氨基烷基（非糖部分）基团的糖苷键连接。这些化合物在葡萄糖胺环上的4或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。还公开了将这些化合物用作辅助剂和免疫效应物质的方法。

  公开号：

  US06355257B1

文献信息

• Aminoalkyl glucosamine phosphate compounds and their use as adjuvants and immunoeffectors
  申请人：Corixa Corporation

  公开号：US06355257B1

  公开（公告）日：2002-03-12

  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.

  描述和声明了一种氨基糖胺磷酸盐化合物，它们是辅助剂和免疫效应物质。这些化合物具有一个2-脱氧-2-氨基葡萄糖与一个氨基烷基（非糖部分）基团的糖苷键连接。这些化合物在葡萄糖胺环上的4或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。还公开了将这些化合物用作辅助剂和免疫效应物质的方法。
• US6355257B1
  申请人：——

  公开号：US6355257B1

  公开（公告）日：2002-03-12
• Synthesis and biological evaluation of a new class of vaccine adjuvants: aminoalkyl glucosaminide 4-phosphates (AGPs)
  作者：David A. Johnson、C. Gregory Sowell、Craig L. Johnson、Mark T. Livesay、David S. Keegan、Michael J. Rhodes、J. Terry Ulrich、Jon R. Ward、John L. Cantrell、Valerie G. Brookshire

  DOI：10.1016/s0960-894x(99)00374-1

  日期：1999.8

  A novel series of acylated omega-aminoalkyl 2-amino-2-deoxy-4-phosphono-beta-D-glucopyranosides (aminoalkyl glucosaminide 4-phosphates) was synthesized and screened for immunostimulant activity. Several of these compounds enhance the production of tetanus toroid-specific antibodies in mice and augment vaccine-induced cytotoxic T cells against EG.7-ova target cells. (C) 1999 Elsevier Science Ltd. Pill rights reserved.