Methyl 4-O-(2-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside | 244076-93-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methyl 4-O-(2-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: Methyl 4-o-(2-o-allyl-beta-d-galactopyranosyl)-beta-d-glucopyranoside；(2R,3R,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl]oxy-2-(hydroxymethyl)-5-prop-2-enoxyoxane-3,4-diol
• CAS: 244076-93-5
• 化学式: C₁₆H₂₈O₁₁
• 分子量: 396.392
• InChiKey: MHQWXJJIBBVFFS-FZVFFMNZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  168
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  Methyl 4-O-(2-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 吡啶 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 6.05h， 生成 Methyl 4-O-(2-O-allyl-6-O-benzoyl-3-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  志贺样毒素1型的二糖和三糖抑制剂的合成及其构效关系

  摘要：

  合成的半乳糖和P k-三糖类似物，其中选定的羟基被O-甲基取代，氨基 脱氧 乙酰氨基报道了脱氧和羧基烷基。这些的能力抑制剂通过固相竞争测定法评估阻断大肠杆菌维毒素1与其哺乳动物细胞表面受体的结合的方法。描述了用于该测定法的生物素化的糖缀合物的合成，其中构建了P k-三糖系链衍生物70并将其共价附接到牛血清白蛋白上，随后是生物素化。半乳糖衍生物4和5含有羧甲基β-半乳糖残基的O --2处的羧基或羧基乙基取代基显示出15-20倍的活性增加甲基糖苷半乳糖。对于相应的羧甲基取代的P k-三糖类似物13，未观察到这种增强的活性。通过与P k-三糖类似物复合的Verotoxin 1的晶体结构合理化抑制数据，并为二聚体的设计提供了见识抑制剂可以利用毒素B亚基的独特结合位点分布。该讨论提供了由有序人扮演的重要角色的另一个示例。水 糖中的分子蛋白质 复合体。

  DOI：

  10.1039/b009685g
• 作为产物：
  描述：

  2,3,6-Tri-O-acetyl-4-O-(3,4,6-tri-O-acetyl-2-O-allyl-β-D-galactopyranosyl)-α-D-glucopyranosyl chloride 以 甲醇 为溶剂， 以67%的产率得到Methyl 4-O-(2-O-allyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Treatment of bacterial dysentery

  摘要：

  本发明涉及与肠道E. coli感染相关的志贺样毒素（SLT）结合的化合物，包括这些化合物的组合物，用于在患者中中和（SLT）的方法，以及用于诊断肠道E. coli感染的方法。这些化合物包括一个核心分子，与多个连接臂结合，这些连接臂又与多个桥接基团结合，这些桥接基团又与两个或三个二糖或三糖基团结合。这些二糖或三糖基团本身就具有与SLTs结合的活性。二糖或三糖的多桥二聚体的存在使得这些化合物相对于二糖或三糖本身具有更高的结合亲和力。这些化合物在及时给患有肠道E. coli感染的患者治疗时，可以抑制该感染进展为溶血性尿毒症综合征（HUS）。

  公开号：

  US05962423A1

文献信息

• Treatment of bacterial infections
  申请人：Governors of the University of Alberta

  公开号：US06310043B1

  公开（公告）日：2001-10-30

  Compounds which bind to toxins associated with enteric bacterial infection, compositions including the compounds, methods for the neutralization of toxins in a patient, and methods for the diagnosis of bacterial and viral infections are disclosed. Toxins which can be bound by the compounds include pentameric toxins, for example SLTs, such as those from salmonella, camylobacter and other bacteria, verotoxins from E. coli, cholera toxin, clostridium difficile toxins A and B, bacterial pili from enteropathogenic E. coli (EPEC) and enterotoxigenic E. coli (ETEC) and viral lectins such as viral hemagglutinins. The compounds include a core molecule bound to a plurality of linker arms, which in turn are bound to a plurality of bridging moieties, which in turn are bound to at least one, and preferably, two or more ligands which bind to the toxin. The presence of a plurality of bridged dimers of the ligands is responsible for the increased binding affinity of the compounds relative to the ligands themselves. In one embodiment, the compounds, when administered in a timely fashion to a patient suffering from enteric E. coli infection, inhibit progression of this infection into hemolytic uremic syndrome (HUS).

  本文披露了与肠道细菌感染相关的毒素结合的化合物，包括这些化合物的组合物，中和患者体内毒素的方法，以及用于诊断细菌和病毒感染的方法。这些化合物能够结合的毒素包括五聚毒素，例如来自沙门氏菌、弯曲杆菌和其他细菌的SLTs，大肠杆菌的毒素，霍乱毒素，难辨梭菌毒素A和B，肠致病性大肠杆菌（EPEC）和肠毒素原性大肠杆菌（ETEC）的细菌纤毛以及病毒凝集素如病毒血凝素。这些化合物包括一个核心分子，与多个连接臂相结合，这些连接臂又与多个桥接基团相结合，这些桥接基团又与至少一个结合毒素的配体相结合，最好是两个或更多个配体。配体的多个桥接二聚体的存在使得这些化合物相对于配体本身具有更高的结合亲和力。在一种实施例中，当及时向患有肠道大肠杆菌感染的患者投与这些化合物时，能够抑制该感染进展为溶血性尿毒症综合征（HUS）。
• TREATMENT OF BACTERIAL INFECTIONS
  申请人：THE GOVERNORS OF THE UNIVERSITY OF ALBERTA

  公开号：EP1102779A2

  公开（公告）日：2001-05-30
• US5962423A
  申请人：——

  公开号：US5962423A

  公开（公告）日：1999-10-05
• US6310043B1
  申请人：——

  公开号：US6310043B1

  公开（公告）日：2001-10-30
• [EN] TREATMENT OF BACTERIAL INFECTIONS<br/>[FR] TRAITEMENT D'INFECTIONS BACTERIENNES
  申请人：UNIV ALBERTA

  公开号：WO2000008467A2

  公开（公告）日：2000-02-17

  Compounds which bind to toxins associated with enteric bacterial infection, compositions including the compounds, methods for the neutralization of toxins in a patient, and methods for the diagnosis of bacterial and viral infections are disclosed. Toxins which can be bound by the compounds include pentameric toxins, for example SLTs, such as those from salmonella, camylobacter and other bacteria, verotoxins from E. coli, cholera toxin, clostridium difficile toxins A and B, bacterial pili from enteropathogenic E. coli (EPEC) and enterotoxigenic E. coli (ETEC) and viral lectins such as viral hemagglutinins. The compounds include a core molecule bound to a plurality of linker arms, which in turn are bound to a plurality of bridging moieties, which in turn are bound to at least one, and preferably, two or more ligands which bind to the toxin. Examples of suitable ligands include di- and for trisaccharide moieties. The di- or tri-saccharide moieties themselves are active in binding to the SLTs. The presence of a plurality of briged dimers of the ligands is responsible for the increased binding affinity of the compounds relative to the ligands themselves. In one embodiment, the compounds, when administered in a timely fashion to a patient suffering from enteric E. coli infection, inhibit progression of this infection into hemolytic uremic syndrome (HUS).