2-(2-Azidoethoxy)ethyl α-D-mannopyranoside | 206659-03-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(2-Azidoethoxy)ethyl α-D-mannopyranoside
• 英文别名: (2S,3S,4S,5S,6R)-2-[2-(2-azidoethoxy)ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 206659-03-2
• 化学式: C₁₀H₁₉N₃O₇
• 分子量: 293.277
• InChiKey: GXRIHNOYMHEVSN-ZJDVBMNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  2-(2-Azidoethoxy)ethyl α-D-mannopyranoside 在 10percent Pd/C 氢气 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 以98%的产率得到2-(2-Aminoethoxy)ethyl α-D-mannopyranoside
  参考文献：
  名称：

  Trivalent α-D-mannoside clusters as inhibitors of type-1 fimbriae-mediated adhesion of Escherichia coli: structural variation and biotinylation

  摘要：

  本文介绍了对三价簇甘露糖苷的结构改造，以进一步阐明大肠杆菌 1 型脂质凝集素的配体偏好。研究人员对两种类型的甘露糖苷进行了改变，一种是改变 2 型甘露糖苷簇的苷元部分，从而得到 27 型甘露糖苷簇；另一种是改变 1 型甘露糖苷簇的间隔长度，从而得到 20-22 型甘露糖苷簇。图中还显示了生物素与 1 型脂质凝集素亲和力最高的簇甘露糖苷的亲和力（33）。在酶联免疫吸附试验（ELISA）中，测试了合成的簇苷作为大肠杆菌与甘露聚糖特异性（1 型纤维凝集素介导的）结合的抑制剂的抑制效力，结果表明，簇 2a 中的结构预组织可以与簇 22 中更大的间隔灵活性很好地结合起来。

  DOI：

  10.1039/b009786l
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 sodium methylate 、 氰化汞 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 1.5h， 生成 2-(2-Azidoethoxy)ethyl α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of Neoglycolipids Containing Oligosaccharides Based on 3,6-Branched-α-D-Mannopyranosides as the Carbohydrate Moieties

  摘要：

  Several oligosaccharides containing 3,6-branched-alpha-D-mannopyranosides were obtained by selective glycosylation of 5-azido-3-oxapentyl alpha-D-mannopyranoside with acetobromosugars. After deacetylation and reduction of the spacer azido group, the oligosaccharides were coupled with the activated hemisuccinate derivatives of cholesterol and 1,2-di-O-alkylglycerol. The neoglycolipids so obtained were characterized by NMR spectroscopy and will be used as liposome coating molecules for targeting entrapped antigens.

  DOI：

  10.1080/07328309808007460

文献信息

• TARGETED NANOPREPARATION OF MANNOSE, AND PREPARATION THEREFOR AND APPLICATION THEREOF
  申请人：CHENGDU RIBOCURE PHARMATECH COMPANY LIMITED

  公开号：US20210196832A1

  公开（公告）日：2021-07-01

  The present invention relates to the field of pharmaceutical preparations, in particular, to a mannose modified targeting nano-preparations, a composition for preparing nano-preparations, a targeting element, a targeting vector, a prepared targeting drug and a preparation method and the application thereof. The described nano-preparations with targeting function is composed of the targeting ligand mannose and its derivatives, nano-preparations and main drug components, and the described targeting material is linked with the spacer material, and then linked with the nano-preparations material to prepare the nano-preparations. The targeting nano-preparations in the present invention has good targetability of mannose receptor, can effectively bond with mannose receptor on target cell. Moreover, the preparation method has universality, can be used for synthesizing a variety of targeting nano-preparations, and is conducive to purification and characterization.

  本发明涉及制药制剂领域，具体地说，涉及一种甘露糖修饰靶向纳米制剂，用于制备纳米制剂的组合物，靶向元素，靶向载体，制备的靶向药物以及其制备方法和应用。所述具有靶向功能的纳米制剂由靶向配体甘露糖及其衍生物、纳米制剂和主要药物成分组成，所述靶向材料与间隔材料连接，然后与纳米制剂材料连接以制备纳米制剂。本发明的靶向纳米制剂具有良好的甘露糖受体靶向性，能够有效地与靶细胞上的甘露糖受体结合。此外，制备方法具有普适性，可用于合成各种靶向纳米制剂，并有利于纯化和表征。
• Synthesis and antibacterial activities of novel tyrocidine A glycosylated derivatives towards multidrug-resistant pathogens
  作者：Yan Zou、Qingjie Zhao、Chunmei Zhang、Liang Wang、Wenjuan Li、Xiang Li、Qiuye Wu、Honggang Hu

  DOI：10.1002/psc.2774

  日期：2015.7

  and functions of peptides and plays a critical role in interacting with or binding to the target molecules. Herein, based on the previously reported method for macrocyclic glycopeptide synthesis, two series of tyrocidine A glycosylated derivatives (1a–f and 2a–f) were synthesized and evaluated for their antibacterial activities to further study the structure and activity relationships (SAR). Biological

  糖基化可以对肽的性质和功能产生多方面的影响，并且在与靶分子相互作用或结合中起关键作用。在此，根据先前报道的大环糖肽合成方法，合成了两个系列的酪氨酸A糖基化衍生物（1a-f和2a-f），并对其抗菌活性进行了评估，以进一步研究其结构和活性关系（SAR）。生物学研究表明，合成的糖基化衍生物对耐甲氧西林的金黄色葡萄球菌和耐万古霉素的肠球菌具有良好的抗菌活性。。SAR研究基于各种聚糖和键联来增强生化特性，从而鉴定出几种有效的抗生素，例如1f，其治疗指数比酪氨酸A大为改善。版权所有©2015欧洲肽协会和John Wiley＆Sons ，Ltd.
• Novel template-assembled oligosaccharide clusters as epitope mimics for HIV-neutralizing antibody 2G12. Design, synthesis, and antibody binding study
  作者：Jingsong Wang、Hengguang Li、Guozhang Zou、Lai-Xi Wang

  DOI：10.1039/b702961f

  日期：——

  The synthesis of a new class of template-assembled oligomannose clusters as the mimics of the epitope of the HIV-neutralizing antibody 2G12 is described. The novel oligomannose clusters were successfully assembled on a cyclic decapeptide template using the Cu(I)-catalyzed 1,3-dipolar cycloaddition of azides to alkynes by introducing four units of a synthetic D1 arm tetrasaccharide (Manα1,2Manα1,2Manα1,3Manα-) of high-mannose N-glycan on one face of the template and two T-helper epitope peptides on the other face of the template. Their binding to human antibody 2G12 was studied using surface plasmon resonance (SPR) technology. It was found that while the synthetic monomeric D1 arm oligosaccharide and its fluorinated derivative interacted with 2G12 only weakly, the corresponding template-assembled oligosaccharide clusters showed high affinity to antibody 2G12, indicating a clear clustering effect in 2G12 recognition. Interestingly, the fluorinated D1 arm cluster, in which the 6-OH of the terminal mannosyl residue was replaced with a fluorine atom, showed a distinct kinetic model in 2G12 binding as compared with the cluster of the natural D1 arm oligosaccharides. The oligosaccharide clusters with varied length of spacer demonstrated different affinity to 2G12, suggesting that an appropriate spatial orientation of the sugar chains in the cluster was crucial for high affinity binding to the antibody 2G12. It was also found that the introduction of two T-helper epitopes onto the template did not affect the structural integrity of the oligomannose cluster. The novel synthetic glycoconjugates represent a new type of immunogen that may be able to raise carbohydrate-specific neutralizing antibodies against HIV-1.

  描述了一种新型模板组装的寡甘露聚糖簇的合成，该簇模仿了HIV中和抗体2G12的表位。这些新颖的寡甘露聚糖簇成功地在一个环状十肽模板上组装，采用了铜(I)催化的叠氮化物与炔烃的1,3-极性环加成反应，通过在模板的一侧引入四个单位的合成D1臂四糖（Manα1,2Manα1,2Manα1,3Manα-）和在另一侧引入两个T辅助表位肽。使用表面等离子共振（SPR）技术研究了它们与人抗体2G12的结合。研究发现，虽然合成的单体D1臂寡糖及其氟化衍生物与2G12的相互作用非常弱，但相应的模板组装的寡糖簇对抗体2G12显示出高亲和力，表明在2G12识别中存在明显的聚集效应。有趣的是，氟化D1臂簇中末端甘露糖残基的6-OH被氟原子取代时，与天然D1臂寡糖簇相比，其在与2G12结合时展现出明显不同的动力学模型。具有不同长度间隔链的寡糖簇对2G12的亲和力表现出不同，表明聚糖链在簇中的适当空间取向对于与抗体2G12的高亲和力结合至关重要。研究还发现，在模板上引入两个T辅助表位并没有影响寡甘露聚糖簇的结构完整性。这些新颖的合成糖 conjugates 代表了一种新型免疫原，可能能够引发针对HIV-1的特异性中和抗体。
• Targeting Bacterial Biofilm: A New LecA Multivalent Ligand with Inhibitory Activity
  作者：Alessandro Palmioli、Paola Sperandeo、Alessandra Polissi、Cristina Airoldi

  DOI：10.1002/cbic.201900383

  日期：2019.12.2

  antibiotic therapies. Infections caused by Pseudomonas aeruginosa are of great concern, especially for immunocompromised and cystic fibrosis patients. P. aeruginosa lectins LecA and LecB are virulence factors and play a key role in establishing biofilm; therefore, inhibition of the function of these proteins has potential in dismantling the bacterium from the protective biofilm environment and in restoring

  细菌性病原体形成生物膜是慢性感染的标志，并与增加的抗生素耐受性有关，这使得病原体难以通过常规抗生素疗法根除。铜绿假单胞菌引起的感染引起了极大的关注，特别是对于免疫功能低下和囊性纤维化患者。铜绿假单胞菌凝集素LecA和LecB是毒力因子，在建立生物膜中起关键作用。因此，抑制这些蛋白质的功能具有从保护性生物膜环境中分解细菌和恢复抗生素活性的潜力。在这里，我们报道了基于半乳糖的树状大分子（Gal18）与LecA结合的NMR特征。此外，我们证明了Gal18分子在体外抑制铜绿假单胞菌生物膜形成的活性。
• Spatially well-defined carbohydrate nanoplatforms: synthesis, characterization and lectin interaction study
  作者：B. J. J. Timmer、M. Abellán Flos、L. Mønster Jørgensen、D. Proverbio、S. Altun、O. Ramström、T. Aastrup、S. P. Vincent

  DOI：10.1039/c6cc06737a

  日期：——

  Two novel dodecasubstituted carbohydrate nanoplatforms have been prepared for use in evaluating the importance of the spatial distribution of carbohydrates in their interaction with lectins.

  已准备了两种新型的十二重取代糖类纳米平台，用于评估糖类在与凝集素相互作用中的空间分布的重要性。