8-azido-3,6-dioxa-octyl β-D-galactopyranoside | 126765-27-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 8-azido-3,6-dioxa-octyl β-D-galactopyranoside
• 英文别名: 2-[2-(2-azidoethoxy)ethoxy]ethyl-β-D-galactopyranoside；2-[2-(2-azidoethoxy)ethoxy]ethoxy-β-D-galactopyranoside；1-azido-3,6-dioxaoct-8-yl-β-D-galactopyranoside；[2-(2-azidoethoxy)ethoxy]ethyl β-D-galactopyranoside；1-O-(2-(2-(2-Azidoethoxy)ethoxy)ethoxy)-beta-D-galactopyranoside；(2R,3R,4S,5R,6R)-2-[2-[2-(2-azidoethoxy)ethoxy]ethoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 126765-27-3
• 化学式: C₁₂H₂₃N₃O₈
• 分子量: 337.33
• InChiKey: ABBZTEUICIJBPU-YBXAARCKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  23
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  10

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  8-azido-3,6-dioxa-octyl β-D-galactopyranoside 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以63%的产率得到(2-[2-(2-aminoethoxy)ethoxy]ethyl) β-D-galactopyranoside
  参考文献：
  名称：

  Carbohydrate conjugation through microwave-assisted functionalization of single-walled carbon nanotubes using perfluorophenyl azides

  摘要：

  Carbohydrate-functionalized single-walled carbon nanotubes (SWNTs) were synthesized using microwave-assisted reaction of perfluorophenyl azide with the nanotubes. The results showed that microwave radiation provides a rapid and effective means to covalently attach carbohydrates to SWNTs, producing carbohydrate-SWNT conjugates for biorecognition. The carbohydrate-functionalized SWNTs were furthermore shown to interact specifically with cognate carbohydrate-specific proteins (lectins), resulting in predicted recognition patterns. The carbohydrate-presenting SWNTs constitute a new platform for sensitive protein-or cell recognition, which pave the way for glycoconjugated carbon nanomaterials in biorecognition applications. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.09.006
• 作为产物：
  描述：

  beta-D-半乳糖五乙酸酯 在 sodium azide 、 三氟化硼乙醚 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 8-azido-3,6-dioxa-octyl β-D-galactopyranoside
  参考文献：
  名称：

  用两亲性Janus Glycodendrimers自组装的可编程聚糖配体模拟生物膜

  摘要：

  加速的模块合成产生了18种两亲性Janus糖树状聚合物，具有由两个或一个碳水化合物头基或具有非碳水化合物亲水性臂的混合构象形成的三种不同拓扑。通过将它们的THF溶液简单地注入到水或缓冲液中，所有Janus化合物就会自组装成均匀，稳定和柔软的单层囊泡，称为糖树状大分子。混合的星座拓扑糖树状大分子被证明在结合植物，细菌和人凝集素方面最有效。具有生物医学相关受体的证据为这种糖类树状小体在靶向药物递送，疫苗和纳米医学的其他领域中的应用提供了有希望的前景。

  DOI：

  10.1002/anie.201403186

文献信息

• Synthesis and Excellent Duplex Stability of Oligonucleotides Containing 2′-Amino-LNA Functionalized with Galactose Units
  作者：Rajesh Kumar、Annika Ries、Jesper Wengel

  DOI：10.3390/molecules22050852

  日期：——

  A convenient method for the preparation of oligonucleotides containing internally-attached galactose and triantennary galactose units has been developed based on click chemistry between 2′-N-alkyne 2′-amino-LNA nucleosides and azido-functionalized galactosyl building blocks. The synthesized oligonucleotides show excellent binding affinity and selectivity towards complementary DNA/RNA strands with an

  基于 2'-N-炔烃 2'-氨基-LNA 核苷和叠氮基功能化的半乳糖基结构单元之间的点击化学，开发了一种制备含有内部连接的半乳​​糖和三触角半乳糖单元的寡核苷酸的便捷方法。合成的寡核苷酸对互补 DNA/RNA 链显示出优异的结合亲和力和选择性，三重修饰变体的解链温度最高可提高 +23.5 °C。
• A One-Step Synthesis of Azide-Tagged Carbohydrates: Versatile ­Intermediates for Glycotechnology
  作者：Lara Mahal、Aditya Sanki

  DOI：10.1055/s-2006-926264

  日期：——

  Herein we describe a simple and practical methodology for accessing both the α-anomers (d-mannose, N-acetyl-d-glucosamine, N-acetyl-d-galactosamine, d-lactose) and α- and β-anomers (d-glucose, d-galactose, l-fucose) of 2′-azidoethyl and azidotriethylene glycol glycosides using free sugars and Dowex 50 (resin) as an efficient catalyst. These azidoalkyl glycosides are increasingly useful synthetic intermediates for glycotechnology.

  本文描述了一种简单实用的方法，能够获取2′-氮杂乙基和氮杂三乙烯二醇糖苷的α-异构体（d-甘露糖、N-乙酰-d-葡萄糖胺、N-乙酰-d-半乳糖胺、d-乳糖）以及α-和β-异构体（d-葡萄糖、d-半乳糖、l-岩藻糖），采用游离糖和Dowex 50（树脂）作为高效催化剂。这些氮杂烷基糖苷在糖科技中越来越成为有用的合成中间体。
• Synthesis of Multivalent Carbohydrate-Centered Glycoclusters as Nanomolar Ligands of the Bacterial Lectin LecA from <i>Pseudomonas aeruginosa</i>
  作者：Marina L. Gening、Denis V. Titov、Samy Cecioni、Aymeric Audfray、Alexey G. Gerbst、Yury E. Tsvetkov、Vadim B. Krylov、Anne Imberty、Nikolay E. Nifantiev、Sébastien Vidal

  DOI：10.1002/chem.201300135

  日期：2013.7.8

  the bacterial lectin LecA with various valencies (from 2 to 4) and linkers. Evaluation of their binding properties towards LecA has been performed by a combination of hemagglutination inhibition assays (HIA), enzyme‐linked lectin assays (ELLA), and isothermal titration microcalorimetry (ITC). Divalent ligands displayed dissociation constants in the sub‐micromolar range and tetravalent ligands displayed

  基于环状寡聚（1→6）-β- D的15个糖簇的家族葡糖胺核心被设计为细菌凝集素LecA的潜在抑制剂，具有不同的化合价（从2到4）和连接子。通过结合血凝抑制试验（HIA），酶联凝集素试验（ELLA）和等温滴定微量量热法（ITC）评估了它们与LecA的结合特性。二价配体在亚微摩尔范围内显示解离常数，四价配体对该凝集素显示低纳摩尔亲和力。链接器的影响也可以得到证明；芳香族部分是与凝集素结合的最佳支架。然后将体外观察到的亲和力与分子模型相关联，以合理化这些糖簇与细菌凝集素的可能结合模式。
• Site-selective modification of proteins for the synthesis of structurally defined multivalent scaffolds
  作者：Lukas M. Artner、Lars Merkel、Nina Bohlke、Figen Beceren-Braun、Christoph Weise、Jens Dernedde、Nediljko Budisa、Christian P. R. Hackenberger

  DOI：10.1039/c1cc16039g

  日期：——

  A combination of classical site-directed mutagenesis, genetic code engineering and bioorthogonal reactions delivered a chemically modified barstar protein with one or four carbohydrates installed at specific residues. These protein conjugates were employed in multivalent binding studies, which support the use of proteins as structurally defined scaffolds for the presentation of multivalent ligands.

  经典的定点突变、遗传密码工程和生物正交反应相结合，产生了在特定残基上安装了一种或四种碳水化合物的化学修饰巴氏星蛋白质。这些蛋白质共轭物被用于多价配体结合研究，支持将蛋白质作为结构明确的支架来呈现多价配体。
• <b>Synthesis of Dodecavalent Fullerene‐Based Glycoclusters and Evaluation of Their Binding Properties towards a Bacterial Lectin</b>
  作者：Samy Cecioni、Vincent Oerthel、Julien Iehl、Michel Holler、David Goyard、Jean‐Pierre Praly、Anne Imberty、Jean‐François Nierengarten、Sébastien Vidal

  DOI：10.1002/chem.201003258

  日期：2011.3.7

  biological processes and particularly in lectin–carbohydrate interactions. The design of high‐affinity ligands of lectins should provide molecules capable of interfering with these biological processes and potentially inhibit bacterial or viral infections. Azide–alkyne “click” chemistry was applied to the synthesis of dodecavalent fullerene‐based glycoclusters. The conjugation could be efficiently performed

  多价在生物过程中，尤其是在凝集素与碳水化合物的相互作用中起着重要作用。凝集素的高亲和力配体的设计应提供能够干扰这些生物学过程并可能抑制细菌或病毒感染的分子。叠氮化物-炔烃“点击”化学方法被用于合成基于十二价富勒烯的糖团。结合可以有效地通过任何一个配偶体上的炔或叠氮化物功能（即六-富勒烯加合物或糖苷）来完成。PA‐IL是一种来自机会性病原菌铜绿假单胞菌的细菌凝集素并参与人体组织糖缀合物的识别。获得的糖簇被评估为PA‐IL的配体，并评估了其与糖基化表面竞争的潜力。通过血凝抑制测定法（HIA），酶联凝集素测定法（ELLA）和表面等离振子共振（SPR）测得的亲和力显示出显着的“糖苷簇效应”，与单价比较时结合力最多可增加12000倍碳水化合物参考探针，具有基于十二价富勒烯的糖簇，尽管根据分析技术有所不同。