2-(5-amino)pentyl-3-deoxy-α-D-manno-oct-2-ulopyranosidonic acid | 1427441-88-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(5-amino)pentyl-3-deoxy-α-D-manno-oct-2-ulopyranosidonic acid
• CAS: 1427441-88-0
• 化学式: C₁₃H₂₅NO₈
• 分子量: 323.343
• InChiKey: KONQUGRMSOBITR-VDWIVTDKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.22
• 重原子数：
  22.0
• 可旋转键数：
  9.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  162.7
• 氢给体数：
  6.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  2-(5-amino)pentyl-3-deoxy-α-D-manno-oct-2-ulopyranosidonic acid 、 (2S,3S,4R)-1-(6-(6’-aminohexyl)-a-D-galactopyranosyl)-2-hexacosanoylaminooctadecane-3,4-diol 、 乙二醇-双(丁二酸 N-羟基琥珀酰亚胺酯) 在 吡啶 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以42%的产率得到(2S,3S,4R)-1-(6-(6’-hexanyl succinamido ethyleneglycol succinimidamido 5-pentanyl α-3”-deoxy-D-manno-oct-2”-ulosonic acid pyranoside)-α-D-galactopyranosyl)-2-hexacosanoylaminooctadecane-3,4-diol
  参考文献：
  名称：

  CARBOHYDRATE-GLYCOLIPID CONJUGATE VACCINES

  摘要：

  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。

  公开号：

  US20150238597A1
• 作为产物：
  描述：

  (2R,3S,4S,6S)-6-((5-(benzyl((benzyloxy)carbonyl)amino)pentyl)oxy)-2-((R)-1,2-diacetoxyethyl)-6-(methoxycarbonyl)-5-(phenylselanyl)tetrahydro-2H-pyran-3,4-diyl diacetate 在 偶氮二异丁腈 、 palladium on activated charcoal 、 氢气 、 三正丁基氢锡 、 溶剂黄146 、 sodium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 甲苯 为溶剂， 反应 141.5h， 生成 2-(5-amino)pentyl-3-deoxy-α-D-manno-oct-2-ulopyranosidonic acid
  参考文献：
  名称：

  [EN] TOTAL SYNTHESIS AND IMMUNOLOGICAL EVALUATION OF SACCHARIDE MOIETIES OF THE LIPOPOLYSACCHARIDE FROM NEISSERIA MENINGITIDIS
  [FR] SYNTHÈSE TOTALE ET ÉVALUATION IMMUNOLOGIQUE DE FRACTIONS SACCHARIDIQUES DU LIPOPOLYSACCHARIDE PROVENANT DE NEISSERIA MENINGITIDIS

  摘要：

  本发明涉及以下通式的单糖35＃（R'=H）、双糖36＃（R'≠H；R''=H）、三糖37＃（R'≠H；R''≠H；R'''=H）和四糖1＃（R'≠H；R''≠H；R'''≠H）的全合成，其中R代表-Y-NH2，Y代表连接剂，R'为H或R''为H或R'''为H或来自脑膜炎奈瑟氏菌的脂多糖。本发明还涉及三糖37＃和四糖1＃，包含至少一个糖1＃、35＃、36＃和37＃的疫苗以及使用这种疫苗用于预防由感染四糖α-GlcNAc-(1→2)-α-Hep-(1→3)-α-Hep-(1→5)-α-Kdo或三糖α-Hep-(1→3)-α-Hep-(1→5)-α-Kdo或α-GlcNAc-(1→2)-α-Hep-(1→3)-α-Hep的细菌引起的疾病，特别是预防由脑膜炎奈瑟氏菌引起的脑膜炎、败血症、肺炎和鼻咽炎。

  公开号：

  WO2013041732A1

文献信息

• Diversity-oriented Synthesis of Inner Core Oligosaccharides of the Lipopolysaccharide of Pathogenic Gram-negative Bacteria
  作者：You Yang、Shunsuke Oishi、Christopher E. Martin、Peter H. Seeberger

  DOI：10.1021/ja401164s

  日期：2013.4.24

  Lipopolysaccharide (LPS) is a potent virulence factor of pathogenic Gram-negative bacteria. To better understand the role of L,PS in host-pathogen interactions and to elucidate the antigenic and immunogenic properties of LPS inner core region, a collection of well-defined L-glycero-D-manno-heptose (Hep) and 3-deoxy-alpha-D-manno-oct-2-ulosonic acid (Kdo)-containing inner core oligosaccharides is required. To address this need, we developed a diversity-oriented approach based on a common orthogonal protected disaccharide Hep-Kdo. Utilizing this new approach, we synthesized a range of LPS inner core oligosaccharides from a variety of pathogenic bacteria including Y. pestis, H. influenzae, and Proteus that cause plague, meningitis, and severe wound infections, respectively. Rapid access to these highly branched core oligosaccharides relied on elaboration of the disaccharide Hep-Kdo core as basis for the elongation with various flexible modules including unique Hep and 4-amino-4-deoxy-beta-L-arabinose (Ara4N) monosaccharides and branched Hep-Hep disaccharides. A regio- and stereoselective glycosylation of Kdo 7,8-diol was key to selective installation of the Ara4N moiety at the 8-hydroxyl group of Kdo moiety of the Hep-Kdo disaccharide. The structure of the LPS inner core oligosaccharides was confirmed by comparison of H-1 NMR spectra of synthetic antigens and isolated fragments. These synthetic LPS core oligosaccharides can be covalently bound to carrier proteins via the reducing end pentyl amine linker, to explore their antigenic and immunogenic properties as well as potential applications such as diagnostic tools and vaccines.