β-L-fucopyranosylmethanol | 3737-65-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-L-fucopyranosylmethanol
• 英文别名: (2R,3S,4R,5S,6S)-2-(hydroxymethyl)-6-methyloxane-3,4,5-triol
• CAS: 3737-65-3
• 化学式: C₇H₁₄O₅
• 分子量: 178.185
• InChiKey: VUWMDLRKEQUSPZ-CQOGJGKDSA-N

物化性质

• 沸点：
  367.1±42.0 °C(Predicted)
• 密度：
  1.402±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  90.2
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  β-L-fucopyranosylmethanol 在 吡啶 、 sodium iodide 作用下， 以 丁酮 为溶剂， 生成 [(2S,3R,4R,5S,6S)-4,5-dibenzoyloxy-6-(iodomethyl)-2-methyloxan-3-yl] benzoate
  参考文献：
  名称：

  Synthesis of a non-charged analogue of guanosyldiphosphofucose

  摘要：

  Methylene sulfonoamide is used as a non-charged surrogate of the diphosphate moiety to prepare an analogue of the fucosyl donor guanosyldiphosphofucose of potential use as inhibitor of fucosyltransferases. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01906-2
• 作为产物：
  描述：

  (1R,2R,6R,7S,9R)-4,4,7,12,12-pentamethyl-3,5,8,11,13-pentaoxatricyclo[7.4.0.02,6]tridecane 在 溶剂黄146 作用下， 以 水 为溶剂， 生成 β-L-fucopyranosylmethanol
  参考文献：
  名称：

  Synthesis of a non-charged analogue of guanosyldiphosphofucose

  摘要：

  Methylene sulfonoamide is used as a non-charged surrogate of the diphosphate moiety to prepare an analogue of the fucosyl donor guanosyldiphosphofucose of potential use as inhibitor of fucosyltransferases. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01906-2

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。
• A Biophysical Study with Carbohydrate Derivatives Explains the Molecular Basis of Monosaccharide Selectivity of the Pseudomonas aeruginosa Lectin LecB
  作者：Roman Sommer、Thomas E. Exner、Alexander Titz

  DOI：10.1371/journal.pone.0112822

  日期：——

  The rise of resistances against antibiotics in bacteria is a major threat for public health and demands the development of novel antibacterial therapies. Infections with Pseudomonas aeruginosa are a severe problem for hospitalized patients and for patients suffering from cystic fibrosis. These bacteria can form biofilms and thereby increase their resistance towards antibiotics. The bacterial lectin LecB was shown to be necessary for biofilm formation and the inhibition with its carbohydrate ligands resulted in reduced amounts of biofilm. The natural ligands for LecB are glycosides of d-mannose and l-fucose, the latter displaying an unusual strong affinity. Interestingly, although mannosides are much weaker ligands for LecB, they do form an additional hydrogen bond with the protein in the crystal structure. To analyze the individual contributions of the methyl group in fucosides and the hydroxymethyl group in mannosides to the binding, we designed and synthesized derivatives of these saccharides. We report glycomimetic inhibitors that dissect the individual interactions of their saccharide precursors with LecB and give insight into the biophysics of binding by LecB. Furthermore, theoretical calculations supported by experimental thermodynamic data suggest a perturbed hydrogen bonding network for mannose derivatives as molecular basis for the selectivity of LecB for fucosides. Knowledge gained on the mode of interaction of LecB with its ligands at ambient conditions will be useful for future drug design.

  细菌对抗生素耐药性的增加是公共卫生的一大威胁，需要开发新型抗菌疗法。铜绿假单胞菌感染是住院病人和囊性纤维化患者面临的一个严重问题。这些细菌会形成生物膜，从而增加对抗生素的耐药性。研究表明，细菌凝集素 LecB 是生物膜形成的必要条件，使用其碳水化合物配体进行抑制可减少生物膜的数量。LecB 的天然配体是 d-甘露糖苷和 l-岩藻糖苷，后者显示出不同寻常的强亲和力。有趣的是，虽然甘露糖苷对 LecB 的配体作用要弱得多，但在晶体结构中，它们确实与蛋白质形成了额外的氢键。为了分析岩藻糖苷中的甲基和甘露糖苷中的羟甲基对结合的贡献，我们设计并合成了这些糖苷的衍生物。我们报告的仿糖抑制剂剖析了其糖类前体与 LecB 的单独相互作用，并深入揭示了 LecB 结合的生物物理学原理。此外，实验热力学数据支持的理论计算表明，甘露糖衍生物的氢键网络是 LecB 对岩藻糖苷具有选择性的分子基础。有关 LecB 与其配体在环境条件下的相互作用模式的知识将有助于未来的药物设计。
• [EN] PHOTODYNAMIC THERAPY AND DIAGNOSIS<br/>[FR] THÉRAPIE ET DIAGNOSTIC PHOTODYNAMIQUES
  申请人：RMW CHO GROUP LTD

  公开号：WO2022112537A1

  公开（公告）日：2022-06-02

  The present invention relates to phyllochlorin analogues and their pharmaceutically acceptable salts, and compositions comprising phyllochlorin analogues and their pharmaceutically acceptable salts. Phyllochlorin analogues and pharmaceutically acceptable salts thereof are suitable for use in photodynamic therapy, cytoluminescent therapy and photodynamic diagnosis, for example, for treating or detecting a tumour, or for antiviral treatment. The present invention also relates to the use of phyllochlorin analogues and pharmaceutically acceptable salts thereof in the manufacture of a phototherapeutic or photodiagnostic agent, and to a method of photodynamic therapy, cytoluminescent therapy or photodynamic diagnosis, for example, for treating or detecting a tumour, or for antiviral treatment.

  本发明涉及叶绿素类似物及其药学上可接受的盐，以及包含叶绿素类似物及其药学上可接受的盐的组合物。叶绿素类似物及其药学上可接受的盐适用于光动力疗法、细胞发光疗法和光动力诊断，例如用于治疗或检测肿瘤或抗病毒治疗。本发明还涉及使用叶绿素类似物及其药学上可接受的盐制造光治疗或光诊断剂，并提供一种光动力疗法、细胞发光疗法或光动力诊断的方法，例如用于治疗或检测肿瘤或抗病毒治疗。
• Synthesis of a non-charged analogue of guanosyldiphosphofucose
  作者：Gérald Carchon、Françoise Chrétien、Philippe Delannoy、André Verbert、Yves Chapleur

  DOI：10.1016/s0040-4039(01)01906-2

  日期：2001.12

  Methylene sulfonoamide is used as a non-charged surrogate of the diphosphate moiety to prepare an analogue of the fucosyl donor guanosyldiphosphofucose of potential use as inhibitor of fucosyltransferases. (C) 2001 Published by Elsevier Science Ltd.