1-O-(β-D-galactopyranosyl)-2-hexacosylamino-D-ribo-1,3,4-octadecanetriol | 163661-57-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 鞘脂
• 英文名称: 1-O-(β-D-galactopyranosyl)-2-hexacosylamino-D-ribo-1,3,4-octadecanetriol
• 英文别名: AGL-583；(2S,3S,4R)-β-D-galactopyranosyl-(1'->1)-2-hexacosanoylaminooctadecan-1,3,4-triol；N-[(1S,2S,3R)-2,3-dihydroxy-1-[[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]heptadecyl]hexacosanamide；N-[(2S,3S,4R)-3,4-dihydroxy-1-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]hexacosanamide
• CAS: 163661-57-2
• 化学式: C₅₀H₉₉NO₉
• 分子量: 858.337
• InChiKey: VQFKFAKEUMHBLV-IGZRNIQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16
• 重原子数：
  60
• 可旋转键数：
  44
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.98
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1-O-(β-D-galactopyranosyl)-2-hexacosylamino-D-ribo-1,3,4-octadecanetriol 在 四丁基氢氧化铵 作用下， 以 正丁醇 为溶剂， 反应 72.0h， 生成 (2S,3S,4R)-2-amino-1-(β-galactopyranosyloxy)octadecan-3,4-diol
  参考文献：
  名称：

  Syntheses of Biotinylated α-Galactosylceramides and Their Effects on the Immune System and CD1 Molecules

  摘要：

  A representative alpha-galactosylceramide (alpha-GalCer), KRN7000, has strong immunostimulatory and antitumor activity. Recent studies demonstrated that KRN7000-pulsed antigen-presenting cells (APC) can activate natural killer T (NKT) cells, a novel T-cell lineage, and CD1d molecules on APC play an important role in the activation of NKT cells. However, it remains unclear whether alpha-GalCers actually bind to CD1d molecules. To address this question, we synthesized three kinds of biotinylated alpha-GalCer and a biotinylated beta-GalCer and found that the biotinylated alpha-GalCers significantly stimulate the proliferation of murine spleen cells, but the biotinylated beta-GalCer does not and that all biotinylated compounds bind to CD1d molecules.

  DOI：

  10.1021/jm990054n
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 3.0h， 以25.9 mg的产率得到1-O-(β-D-galactopyranosyl)-2-hexacosylamino-D-ribo-1,3,4-octadecanetriol
  参考文献：
  名称：

  新型 1,2-反式鞘糖脂抗真菌活性的合成与生物学评价

  摘要：

  描述了一系列 1,2-反式糖鞘脂 (GSL) 对白色念珠菌、近平滑念珠菌和热带念珠菌的抗真菌活性的合成和体外生物学评价。初步研究表明，GSLs的糖基种类影响了它们对三种念珠菌的抗真菌活性和选择性，渗透性可能不是之前假设的影响其抗真菌特性的唯一参数，这将为理解抗真菌作用提供新的线索。这些类型的化合物的配置文件。

  DOI：

  10.1002/ardp.201000335

文献信息

• CARBOHYDRATE-GLYCOLIPID CONJUGATE VACCINES
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：US20150238597A1

  公开（公告）日：2015-08-27

  The present invention relates to the field of synthesizing and biologically evaluating of a novel class of carbohydrate-based vaccines. The new vaccines consist of a multi-modular structure which allows applying the vaccine to a whole variety of pathogenes. This method allows preparing vaccines against all pathogens expressing immunogenic carbohydrate antigens. As conjugation of antigenic carbohydrates to proteins is not required the conjugate vaccine is particularly heat stable. No refrigeration is required, a major drawback of protein-based vaccines.

  本发明涉及合成和生物评价一种新型基于碳水化合物的疫苗的领域。这种新疫苗由多模块结构组成，可以将疫苗应用于各种病原体。该方法允许制备针对所有表达免疫原碳水化合物抗原的病原体的疫苗。由于不需要将抗原碳水化合物与蛋白质结合，所以结合疫苗尤其耐热稳定。无需冷藏，这是基于蛋白质的疫苗的一个主要缺点。
• Synthetic vaccines against Streptococcus pneumoniae
  申请人：Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.

  公开号：EP2845860A1

  公开（公告）日：2015-03-11

  The present invention relates to the total synthesis of saccharide structures contained in the capsular polysaccharide of Streptococcus pneumoniae type 1, to glycoconjugates containing said saccharide structures obtained by total synthesis and to use of such glycoconjugates and pharmaceutical compositions thereof in the immunization against diseases associated with bacteria containing said saccharide structures in their capsular polysaccharide, and more specifically associated with Streptococcus pneumoniae.

  本发明涉及对肺炎链球菌1型胶囊多糖中含有的糖结构进行全合成，以及通过全合成获得含有该糖结构的糖蛋白结合物，以及利用这种糖蛋白结合物和其制剂在免疫接种中用于预防与含有这种糖结构的细菌相关的疾病，更具体地与肺炎链球菌相关。
• [EN] VACCINES AGAINST STREPTOCOCCUS PNEUMONIAE SEROTYPE 8<br/>[FR] VACCINS CONTRE STREPTOCOCCUS PNEUMONIAE SÉROTYPE 8
  申请人：MAX PLANCK GES ZUR FÖRDERUNG DER WISSENSCHAFTEN E V

  公开号：WO2016046420A1

  公开（公告）日：2016-03-31

  The present invention relates to synthetic saccharides of general formula (I) that are related to Streptococcuspneumoniae serotype 8 capsular polysaccharide, conjugates thereof and the use of said saccharides and conjugates for raising a protective immune response in a human and/or animal host. Furthermore, the synthetic saccharide structures of general formula (I) are useful as marker in immunological assays for detection of antibodies against Streptococcuspneumoniae bacteria.

  本发明涉及一般式（I）的合成糖苷，与肺炎链球菌8型蒽聚糖有关，以及它们的结合物，以及利用所述糖苷和结合物在人类和/或动物宿主中引发保护性免疫反应。此外，一般式（I）的合成糖苷结构可用作免疫学检测中的标记，用于检测针对肺炎链球菌细菌的抗体。
• Novel synthetic C-glycolipids, their synthesis and use to treat infections, cancer and autoimmune diseases
  申请人：Tsuji Moriya

  公开号：US20050222048A1

  公开（公告）日：2005-10-06

  The invention is directed to novel compounds of formulae (I), (II) and (III): wherein X is O or NH; R 3 is OH or a monosaccharide and R 4 is hydrogen, or R 3 is hydrogen and R 4 is OH or a monosaccharide; R 5 is hydrogen or a monosaccharide; and pharmaceutically acceptable salts or esters thereof. The invention is also directed to the use of the compounds both directly and as immune adjuvants for treating cancer, infectious diseases and autoimmune diseases. The invention is also directed to syntheses of the intermediates which can be used to make these novel compounds.

  该发明涉及以下化合物的新颖化合物：其中X为O或NH；R3为OH或单糖，R4为氢，或R3为氢，R4为OH或单糖；R5为氢或单糖；以及其药用盐或酯。该发明还涉及这些化合物的直接使用以及作为免疫佐剂用于治疗癌症、传染病和自身免疫疾病。该发明还涉及合成这些中间体的方法，这些中间体可用于制备这些新颖化合物。
• Ceramide derivatives as modulators of immunity and autoimmunity
  申请人：Porcelli A. Steven

  公开号：US20060052316A1

  公开（公告）日：2006-03-09

  α-Galactosylceramides and glycosylceramides (“ceramide-like glycolipids”) that modulate NK T cells. The ceramide-like glycolipids vary in the cytokines induced in NK T cells and vary in the antigen-presenting cells that are capable of efficiently presenting the compounds to NK T cells. Pharmaceutical compositions of the ceramide-like glycolipids are provided, as are pharmaceutical compositions of the ceramide-like glycolipids combined with dendritic cells. Methods utilizing the ceramide-like glycolipids in vaccines, to activate NK T cells, to stimulate the immune system, and to treat mammals are also provided. The invention also provides methods of evaluating a compound for its ability to activate an NK T cell in the presence of a cell expressing a CD1d protein.

  α-半乳糖基神经酰胺和糖基神经酰胺（“类神经酰胺糖脂”），调节NK T细胞。这些类神经酰胺糖脂在NK T细胞中诱导的细胞因子中有所不同，并且在有效呈递这些化合物给NK T细胞的抗原呈递细胞中也有所不同。提供了含有类神经酰胺糖脂的药物组合物，以及与树突状细胞结合的类神经酰胺糖脂的药物组合物。还提供了利用这些类神经酰胺糖脂制备疫苗、激活NK T细胞、刺激免疫系统和治疗哺乳动物的方法。本发明还提供了评估化合物在表达CD1d蛋白的细胞存在下激活NK T细胞能力的方法。