2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]ethyl 4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-2-deoxy-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]ethyl 4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-2-deoxy-β-D-glucopyranoside
• 英文别名: 2-[(R)-3-Tetradecanoyloxytetradecanoylamino]ethyl 2-Deoxy-4-O-phosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranoside；2-[(R)-3-tetradecanoyloxytetradecanoylamino]ethyl 4-O-phosphono-3-O-[(R)-3-tetradecanoyloxytetradecanoyl]-2-deoxy-2-[(R)-3-tetradecanoyloxytetradecanoylamino]-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-2-(hydroxymethyl)-3-phosphonooxy-5-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]-6-[2-[[(3R)-3-tetradecanoyloxytetradecanoyl]amino]ethoxy]oxan-4-yl] (3R)-3-tetradecanoyloxytetradecanoate
• 化学式: C₉₂H₁₇₅N₂O₁₇P
• 分子量: 1612.38
• InChiKey: VBDKCMNKBLYLIY-OHAKVTJVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  31.3
• 重原子数：
  112
• 可旋转键数：
  88
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  269
• 氢给体数：
  5
• 氢受体数：
  17

反应信息

• 作为产物：
  描述：

  2-[(R)-3-tetradecanoyloxytetradecanoylamino]ethyl 2-deoxy-4-O-diphenylphosphono-3-O-[(R)-3-tetradecanoyoxytetradecanoyl]-2-[(R)-3-tetradecanoyoxytetradecanoylamino]-β-D-glucopyranoside 在 platinum(IV) oxide 氢气 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 生成 2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]ethyl 4-O-phosphono-3-O-[(R)-3-(tetradecanoyloxy)tetradecanoyl]-2-[(R)-3-(tetradecanoyloxy)tetradecanoylamino]-2-deoxy-β-D-glucopyranoside
  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。
• Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors, and intermediates therefor
  申请人：Johnson A. David

  公开号：US20050107600A1

  公开（公告）日：2005-05-19

  This invention relates to processes for production of alkylamino glucosaminide phosphate compounds, and of disaccharide compounds, including various novel intermediates and intermediate processes. In one aspect, glycosyl halides are produced by reaction of an O-silyl glycoside with a dihalomethyl alkyl ether.

  这项发明涉及生产烷基氨基葡糖氨磷酸化合物和二糖化合物的过程，包括各种新颖中间体和中间过程。在一个方面，通过将O-硅糖苷与二卤甲基烷醚反应来生产糖基卤化物。
• PROCESSES FOR THE PRODUCTION OF AMINOALKYL GLUCOSAMINIDE PHOSPHATE AND DISACCHARIDE IMMUNOEFFECTORS, AND INTERMEDIATES THEREFOR
  申请人：Johnson A. David

  公开号：US20080033155A1

  公开（公告）日：2008-02-07

  This invention relates to processes for production of alkylamino glucosaminide phosphate compounds, and of disaccharide compounds, including various novel intermediates and intermediate processes. In one aspect, glycosyl halides are produced by reaction of an O-silyl glycoside with a dihalomethyl alkyl ether.

  本发明涉及生产烷基氨基葡糖氨磷酸化合物和二糖化合物的过程，包括各种新的中间体和中间过程。在一个方面，通过将O-硅糖苷与二卤甲基烷醚反应来产生糖基卤化物。
• Multivalent Pneumococcal Polysaccharide-Protein Conjugate Composition
  申请人：Wyeth LLC

  公开号：EP2425851A1

  公开（公告）日：2012-03-07

  An immunogenic composition having 13 distinct polysaccharide-protein conjugates and optionally, an aluminum-based adjuvant, is described. Each conjugate contains a capsular polysaccharide prepared from a different serotype of Streptococcus pneumoniae (1, 3, 4, 5, 6A, 6B, 7F, 9V, 14, 18C, 19A, 19F and 23F) conjugated to a carrier protein. The immunogenic composition, formulated as a vaccine, increases coverage against pneumococcal disease in infants and young children globally, and provides coverage for serotypes 6A and 19A that is not dependent on the limitations of serogroup cross-protection.

  本文描述了一种具有 13 种不同的多糖-蛋白共轭物和铝基佐剂的免疫原性组合物。每种共轭物都含有由不同血清型的肺炎链球菌（1、3、4、5、6A、6B、7F、9V、14、18C、19A、19F 和 23F）制备的荚膜多糖与载体蛋白共轭。这种免疫原性组合物配制成疫苗后，可在全球范围内提高婴幼儿肺炎球菌疾病的免疫覆盖率，并提供不受血清群交叉保护限制的血清型 6A 和 19A 的免疫覆盖率。
• IMMUNOGENIC GLYCOPROTEIN CONJUGATES
  申请人：Pfizer Inc.

  公开号：EP3443983A1

  公开（公告）日：2019-02-20

  The present invention relates generally to glycoconjugates comprising a saccharide covalently conjugated to a carrier protein through a spacer containing ((2-oxoethyl)thio)). In an aspect the invention provides oxo-eT linked glycoconjugates comprising a saccharide covalently conjugated to a carrier protein through a ((2-oxoethyl)thio) spacer having the formula (I): wherein : A is a group (C=X)m wherein X is S or O and m is 0 or 1; B is a bond, O, or CH2; and when m is 0, B can also be (C=O); R is a C2-C16 alkylene, C2-C16 heteroakylene, NH-C(=O)-C2-C16 alkylene, or NH-C(=O)-C2-C16 heteroakylene, wherein said alkylene and heteroalkylene are optionally substituted by 1, 2 or 3 groups independently selected from COOR' where R' is selected from H, methyl, ethyl or propyl. The invention further relates to immunogenic compositions comprising such glycoconjugates, and to methods for the preparation and use of such glycoconjugates and immunogenic compositions.

  本发明一般涉及糖共轭物，该糖共轭物包括通过含有((2-氧代乙基)硫)的间隔物与载体蛋白共价连接的糖。）在一个方面，本发明提供了氧化-eT 连接的糖结合物，该糖结合物包含通过含有式（I）的（(2-氧代乙基)硫代）间隔物与载体蛋白共价连接的糖： 其中 ： A 是基团 (C=X)m，其中 X 是 S 或 O，m 是 0 或 1； B 是键、O 或 CH2；当 m 为 0 时，B 也可以是 (C=O)； R是C2-C16亚烷基、C2-C16杂亚烷基、NH-C(=O)-C2-C16亚烷基或NH-C(=O)-C2-C16杂亚烷基，其中所述亚烷基和杂亚烷基任选被1、2或3个独立选自COOR'的基团取代，其中R'选自H、甲基、乙基或丙基。 本发明进一步涉及包含这种糖结合物的免疫原性组合物，以及制备和使用这种糖结合物和免疫原性组合物的方法。