N-[(R)-3-dodecanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-2-[(R)-3-dodecanoyloxytetradecanoylamino]-3-O-[(R)-3-dodecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-L-serine benzyl ester | 216013-95-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(R)-3-dodecanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-2-[(R)-3-dodecanoyloxytetradecanoylamino]-3-O-[(R)-3-dodecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-L-serine benzyl ester
• 英文别名: [(2R,3R,4R,5S,6R)-5-diphenoxyphosphoryloxy-3-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-2-[(2S)-2-[[(3R)-3-dodecanoyloxytetradecanoyl]amino]-3-oxo-3-phenylmethoxypropoxy]-6-(hydroxymethyl)oxan-4-yl] (3R)-3-dodecanoyloxytetradecanoate
• CAS: 216013-95-5
• 化学式: C₁₀₆H₁₇₇N₂O₁₉P
• 分子量: 1814.55
• InChiKey: KBFFOCPMQMAINO-JPMLXHGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  34.2
• 重原子数：
  128
• 可旋转键数：
  90
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  273
• 氢给体数：
  3
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  N-[(R)-3-dodecanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-2-[(R)-3-dodecanoyloxytetradecanoylamino]-3-O-[(R)-3-dodecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-L-serine benzyl ester 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-3-Dodecanoyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-2-[(S)-2-carboxy-2-((R)-3-dodecanoyloxy-tetradecanoylamino)-ethoxy]-5-(diphenoxy-phosphoryloxy)-3-((R)-3-dodecanoyloxy-tetradecanoylamino)-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
  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：

  3-dodecanoyloxytetradecanoic acid 、 (R)-3-Dodecanoyloxy-tetradecanoic acid (2R,3R,4R,5S,6R)-3-amino-2-[(S)-2-benzyloxycarbonyl-2-((R)-3-dodecanoyloxy-tetradecanoylamino)-ethoxy]-5-(diphenoxy-phosphoryloxy)-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 二氯甲烷 为溶剂， 生成 N-[(R)-3-dodecanoyloxytetradecanoyl]-O-[2-deoxy-4-O-diphenylphosphono-2-[(R)-3-dodecanoyloxytetradecanoylamino]-3-O-[(R)-3-dodecanoyloxytetradecanoyl]-β-D-glucopyranosyl]-L-serine benzyl ester
  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

文献信息

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

  公开号：US20030199460A1

  公开（公告）日：2003-10-23

  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. Compositions and 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酯（AGP）化合物，这些化合物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）基团在糖苷键中连接的结构。这些化合物在葡萄糖氨基糖环的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，同时也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作为辅助剂和免疫效应物质使用的组合物和方法。
• AMINOALKYL GLUCOSAMINE PHOSPHATE COMPOUNDS AND THEIR USE AS ADJUVANTS AND IMMUNOEFFECTORS
  申请人：CORIXA CORPORATION

  公开号：EP0983286B1

  公开（公告）日：2004-07-28
• US6113918A
  申请人：——

  公开号：US6113918A

  公开（公告）日：2000-09-05
• US6355257B1
  申请人：——

  公开号：US6355257B1

  公开（公告）日：2002-03-12
• US6764840B2
  申请人：——

  公开号：US6764840B2

  公开（公告）日：2004-07-20