2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside | 142072-11-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
• 英文别名: 1-(2-azidoethyl)-2-acetamido-3,4,6-tri-O-acetyl-β-D-glucopyranoside；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-(2-azidoethoxy)oxan-2-yl]methyl acetate
• CAS: 142072-11-5
• 化学式: C₁₆H₂₄N₄O₉
• 分子量: 416.388
• InChiKey: AZZGNJWMBPFQOP-OXGONZEZSA-N

物化性质

• 熔点：
  149 °C
• 闪点：
  -33℃

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  29
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  141
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 、 溶剂黄146 为溶剂， 反应 24.0h， 以35%的产率得到2-aminoethyl 3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Site-selective depurination by a periodate-dependent deoxyribozyme

  摘要：

  一种脱氧核酶被鉴定为能够介导其5′-末端鸟苷酸的位点选择性去嘌呤化，使用过氧酸根离子（IO4–）作为必需的辅因子。

  DOI：

  10.1039/b704507g
• 作为产物：
  描述：

  β-D-葡萄糖胺五乙酸酯 在 sodium azide 、 四丁基碘化铵 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 15.25h， 生成 2-azidoethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Glycoclusters as lectin inhibitors: comparative analysis on two plant agglutinins with different folding as a step towards rules for selectivity

  摘要：

  The emerging physiological significance of carbohydrate (glycan) protein (lectin) recognition engenders the interest to design synthetic inhibitors with a high level of selectivity among natural sugar receptors. Plant agglutinins are common models to determine structure activity relationships. Focussing on the contribution of valency towards selectivity, copper-catalysed azide (sugar derivative)-alkyne (scaffold) cycloaddition yielded a panel of 10 bi- to tetravalent glycoclusters with N-acetylglucosamine as the bioactive headgroup. They were introduced into assays using (neo)glycoproteins and cell surfaces as platforms to study carbohydrate-dependent lectin binding. The ability of the bivalent compounds, which exhibit a distance profile of the sugar headgroups of about 16-21 angstrom, for intramolecular bridging of two contact sites from the eight hevein domains of wheat germ agglutinin led to comparatively high enhancements of inhibitory potency relative to a tetrameric leguminous lectin (distance profile of 50-70 angstrom between sugar-specific sites), especially for a beta-S-glycoside. The extent of inhibition at fixed concentrations of the sugar depended on the type of matrix used for the assay. Increases to tri- and tetravalency played a less important role than the anomeric position to keep cross-reactivity low, these tested topologies enabling cross-linking for both lectins. The potential for cis-interactions (intramolecular interactions), with glycoclusters serving as molecular rulers, is suggested to help designing selective blocking reagents. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.07.020

文献信息

• Preparation of oligosaccharides by homogenous enzymatic synthesis and solid phase extraction
  作者：Wenjun Wang、Chen Jin、Lina Guo、Yu Liu、Yue Wan、Xin Wang、Lei Li、Wei Zhao、Peng George Wang

  DOI：10.1039/c1cc13293h

  日期：——

  This communication describes a method for enzymatic preparation of bioactive glycans, which integrated the high-efficiency of homogenous phase enzymatic reaction and fast separation of solid phase extraction.

  该交流描述了一种酶法制备生物活性聚糖的方法，该方法集高效率的均相酶促反应和固相萃取的快速分离于一体。
• Synthesis of oligosaccharides related to the HNK-1 antigen. 5. Synthesis of a sulfo-mimetic of the HNK-1 antigenic trisaccharide
  作者：E. V. Sukhova、A. V. Dubrovskii、Yu. E. Tsvetkov、N. E. Nifantiev

  DOI：10.1007/s11172-007-0258-y

  日期：2007.8

  Abstract2-Aminoethyl 3,6-di-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→4)-2-acetamido-2-deoxy-β-D-glucopyranoside, which is the sulfo-mimetic of the antigenic trisaccharide HNK-1, and the corresponding monosulfates, viz., 2-aminoethyl 3-O-sulfo-and 2-aminoethyl 6-O-sulfo-β-D-glucopyranosyl-(1→3)-β-D-galactopyranosyl-(1→ 4)-2-acetamido-2-deoxy-β-D-glucopyranosides, were synthesized. 2-Azidoethyl

  摘要2-氨基乙基3,6-二-O-磺基-β-D-吡喃葡萄糖基-(1→3)-β-D-吡喃半乳糖基-(1→4)-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷，它是抗原性三糖 HNK-1 的磺基模拟物，以及相应的单硫酸盐，即 2-氨基乙基 3-O-磺基-和 2-氨基乙基 6-O-磺基-β-D-吡喃葡萄糖基-（1 →3)-β-D-吡喃半乳糖基-(1→4)-2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷被合成。2-叠氮乙基 2,4-二-O-苯甲酰基-β-D-吡喃葡萄糖基-(1→3)-2,4,6-三-O-苯甲酰基-β-D-吡喃半乳糖基-(1→4)-2 -acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glupyranoside 作为硫酸化三糖的常见前体。该化合物是根据 [2+1] 模式从单糖前体合成的：3,6-二-O-乙酰基-2,4-二-O-苯甲酰基-D-吡喃葡萄糖基三氯乙酰亚胺，烯丙基
• Synthesis and Characterization of Novel Fluoro-glycosylated Porphyrins that can be Utilized as Theranostic Agents
  作者：Katriann Arja、Mathias Elgland、Hanna Appelqvist、Peter Konradsson、Mikael Lindgren、K. Peter R. Nilsson

  DOI：10.1002/open.201800020

  日期：2018.7

  characterization of heterobifunctional glycoconjugated porphyrins with two different sugar moieties, a common monosaccharide at three sites, and a 2‐fluoro‐2‐deoxy glucose (FDG) moiety at the fourth site are presented. The fluoro‐glycoconjugated porphyrins exhibit properties for multimodal imaging and photodynamic therapy, as well as specificity towards cancer cells. We foresee that our findings might aid in the

  具有用于各种成像技术的模态以及治疗活性的小分子必不可少，因为此类分子提供了同时进行诊断和靶向治疗的机会，即所谓的治疗法。在这方面，已证明糖卟啉可用作治疗癌症以及非癌性疾病的治疗药物。本文介绍了具有两个不同糖部分，三个位点的常见单糖和第四个位点的2-氟-2-脱氧葡萄糖（FDG）部分的异双功能糖共轭卟啉的合成与表征。氟糖缀合的卟啉具有多模态成像和光动力疗法的特性，以及对癌细胞的特异性。
• Photo-Click Immobilization on Quartz Crystal Microbalance Sensors for Selective Carbohydrate−Protein Interaction Analyses
  作者：Oscar Norberg、Lingquan Deng、Teodor Aastrup、Mingdi Yan、Olof Ramström

  DOI：10.1021/ac102781u

  日期：2011.2.1

  A photoclick method based on azide photoligation and Cu-catalyzed azide−alkyne cycloaddition has been evaluated for the immobilization of carbohydrates to polymeric materials. The biomolecular recognition properties of the materials have been investigated with regard to applicable polymeric substrates and selectivity of protein binding. The method was used to functionalize a range of polymeric surfaces (polystyrene, polyacrylamide, poly(ethylene glycol), poly(2-ethyl-2-oxazoline), and polypropene) with various carbohydrate structures (based on α-d-mannose, β-d-galactose, and N-acetyl-β-d-glucosamine). The functionalized surfaces were evaluated in real-time studies of protein−carbohydrate interactions using a quartz crystal microbalance flow-through system with a series of different carbohydrate-binding proteins (lectins). The method proved to be robust and versatile, resulting in a range of efficient sensors showing high and predictable protein selectivities.

  一种基于叠氮光联接和铜催化的叠氮−炔烃环加成的光点击方法已被评估用于将碳水化合物固定到聚合物材料上。对材料的生物分子识别特性进行了研究，关注适用的聚合物底物和蛋白质结合的选择性。该方法用于功能化多种聚合物表面（聚苯乙烯、聚丙烯酰胺、聚（乙二醇）、聚（2-乙基-2-噁唑啉）和聚丙烯），以及多种碳水化合物结构（基于α-d-甘露糖、β-d-半乳糖和N-乙酰-β-d-葡萄糖胺）。在实时蛋白−碳水化合物相互作用研究中，使用了一种石英晶体微天平流动系统，测试了一系列不同的结合碳水化合物的蛋白质（讲糖蛋白）。该方法被证明是稳健且多功能的，产生了一系列高效传感器，显示出高且可预测的蛋白选择性。
• Solid-Phase Enzymatic Synthesis of a Sialyl Lewis X Tetrasaccharide on a Sepharose Matrix
  作者：O. Blixt、T. Norberg

  DOI：10.1021/jo980074h

  日期：1998.4.1

  different linker lengths. Enzymatic galactosylation of these with beta-(1-4)-galactosyltransferase and UDP-galactose gave yields varying between 70 and 98%, and there was a clear correlation between linker length and yield. A GlcNAc Sepharose with a long linker was then used in a solid-phase synthesis of a sialyl Le x tetrasaccharide. The three required enzymes (galactosyl-, sialyl, and fucosyltransferase)

  由环氧琼脂糖6B首先与1,8-二氨基-3,6-二氧杂辛烷反应，然后与二乙氧基-3-环丁烯-1,2-二酮（方酸二乙酯）反应，制得具有不同连接臂长度的硫代吡啶基琼脂糖）和1,8-二氨基-3,6-二氧杂辛烷在几个循环中，然后使获得的氨基琼脂糖与硫代丁内酯和2,2'-二硫代吡啶相继反应。使硫代吡啶基琼脂糖与葡糖胺衍生物2-（3'-巯基丁酰氨基）乙基2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖苷反应，得到具有不同接头长度的GlcNAc琼脂糖。用β-（1-4）-半乳糖基转移酶和UDP-半乳糖对它们进行酶促半乳糖基化，产率在70％到98％之间变化，并且接头长度和产率之间存在明显的相关性。然后将具有长接头的GlcNAc琼脂糖用于唾液酸Le x四糖的固相合成中。使三种必需的酶（半乳糖基，唾液酸和岩藻糖基转移酶）和核苷酸糖与GlcNAc Sepharose连续反应，在用DTT将Sepharose裂解后，纯化后得到的游离唾液酸Le