azidoethylglucose | 852568-95-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: azidoethylglucose
• 英文别名: 2'-azidoethyl-α-D-glucopyranoside；AzEG；(2S,3R,4S,5S,6R)-2-(2-azidoethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 852568-95-7
• 化学式: C₈H₁₅N₃O₆
• 分子量: 249.224
• InChiKey: VGCOVRUENPCVTD-CBQIKETKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  114
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  azidoethylglucose 在 吡啶 、 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 水 、 copper diacetate 、 sodium 、 溶剂黄146 、 sodium ascorbate 作用下， 以 甲醇 、 二乙二醇二甲醚 、 水 为溶剂， 反应 2.0h， 生成 L-γ-glutamyl-S-[1-[2-[(6-deoxy-6-fluoro-α-D-glucopyranosyl)oxy]ethyl]-1H-1,2,3-triazol-4-yl]-L-cysteinylglycine
  参考文献：
  名称：

  ‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC

  摘要：

  半胱氨酸肽通过Cu(I)催化的叠氮化物-炔烃环加成(CuAAC)实现了"点击"糖基化，产率良好。此方法中，肽通过半胱氨酸残基的直接炔基化进行官能化，使其可用于与具有gluco、manno和galacto构型的合适叠氮化糖（自由或保护状态）进行CuAAC反应。在所获得的自由和保护型糖肽中，一系列"glycoRGD"肽被制备并进行了体外血小板聚集测试，结果显示伪糖基化的黏附序列降低了IC50值，从而可能改善体内药代动力学特性。©2014 Elsevier Ltd. 保留所有权利。

  DOI：

  10.1016/j.bmc.2014.09.056
• 作为产物：
  描述：

  a-无水葡萄糖酯 在 sodium azide 、 sodium iodide 作用下， 以 水 为溶剂， 反应 4.0h， 生成 azidoethylglucose
  参考文献：
  名称：

  DRUG-LIGAND CONJUGATES, SYNTHESIS THEREOF, AND INTERMEDIATES THERETO

  摘要：

  本发明涉及合成式I化合物或其药用可接受盐的方法：其中X、Alk1、Alk2和W各自如本文所定义和描述。

  公开号：

  US20130190475A1

文献信息

• [EN] BINDING-SITE MODIFIED LECTINS AND USES THEREOF<br/>[FR] LECTINES DE SITE DE LIAISON MODIFIÉES ET USAGE CORRESPONDANT
  申请人：SMARTCELLS INC

  公开号：WO2010088261A1

  公开（公告）日：2010-08-05

  In one aspect, the disclosure provides cross-linked materials that include multivalent lectins with at least two binding sites for glucose, wherein the lectins include at least one covalently linked affinity ligand which is capable of competing with glucose for binding with at least one of said binding sites; and conjugates that include two or more separate affinity ligands bound to a conjugate framework, wherein the two or more affinity ligands compete with glucose for binding with the lectins at said binding sites and wherein conjugates are cross-linked within the material as a result of non-covalent interactions between lectins and affinity ligands on different conjugates. These materials are designed to release amounts of conjugate in response to desired concentrations of glucose. Depending on the end application, in various embodiments, the conjugates may also include a drug and/or a detectable label.

  在一个方面，该公开提供了包括多价凝集素的交联材料，其中该多价凝集素具有至少两个葡萄糖结合位点，其中该凝集素包括至少一个与亲和配体共价连接的亲和配体，该亲和配体能够与至少一个所述结合位点中的葡萄糖竞争结合；以及包括绑定到共轭框架的两个或更多个独立亲和配体的共轭物，其中这两个或更多个亲和配体与葡萄糖在所述结合位点上与凝集素竞争结合，其中由于不同共轭物上的凝集素和亲和配体之间的非共价相互作用，共轭物在材料内交联。这些材料旨在根据所需葡萄糖浓度释放共轭物的量。根据最终应用，在各种实施例中，共轭物还可以包括药物和/或可检测标记。
• GLYCOSIDE DERIVATIVES, PREPARATION THEREOF AND USE THEREOF AS PROSTHETIC GROUPS
  申请人：UNIVERSITÉ DE LORRAINE

  公开号：US20160031923A1

  公开（公告）日：2016-02-04

  The present invention relates to glycoside-derived compounds, to the processes for preparing same and to the use thereof as prosthetic groups for radiolabelling biomolecules. These compounds are co-azido-alkyl 6-deoxy-6-[ 18 F]-fluoroglycosides of formula (I), in which: k is equal to 2 or 3; n is an integer between 1 and 5; R is independently H or a C 1 -C 5 alkyl group, m being an integer between 0 and 2 if k=2 and m between 0 and 3 if k=3; and X is chosen from the group comprising O, S, CH 2 and NR′, in which R′ is independently a C 1 -C 5 alkyl group or an aryl group, including all the stereoisomers thereof.

  本发明涉及糖苷衍生化合物，制备这些化合物的方法以及将其用作放射标记生物分子的假体基团。这些化合物是公式（I）的共氮烷基6-去氧-6-[18F]-氟糖苷，其中：k等于2或3；n是1到5之间的整数；R独立地是H或C1-C5烷基，如果k=2，则m是0到2之间的整数，如果k=3，则m是0到3之间的整数；X从包括O、S、CH2和NR′的群体中选择，其中R′独立地是C1-C5烷基或芳基，包括所有的立体异构体。
• Development of 6-[¹⁸F]fluoro-carbohydrate-based prosthetic groups and their conjugation to peptides via click chemistry
  作者：Charlotte Collet、Fatiha Maskali、Alexandra Clément、Françoise Chrétien、Sylvain Poussier、Gilles Karcher、Pierre-Yves Marie、Yves Chapleur、Sandrine Lamandé-Langle

  DOI：10.1002/jlcr.3362

  日期：2016.2

  This work describes the development of new 6-[18F]fluoro-carbohydrate-based prosthetic groups equipped with an azido arm that are able to participate in copper(I)-catalyzed cycloadditions for 18F labeling of biomolecules under mild conditions. The radiolabeling in high radiochemical yields (up to 68 ± 6%) of these different prosthetic groups is presented. The flexibility of the azido arm introduced on the carbohydrate moieties allows efficient click reactions with different alkyne functionalized peptides such as gluthation or Arg-Gly-Asp derivatives in order to prepare glycopeptides. The radiosyntheses of 18F-labeled glycopeptides proceed in high radiochemical yields (up to 76%) in an automated process with excellent radiochemical purity. The addition of a sugar moiety on peptides should enhance the bioavailability, pharmacokinetic, and in vivo clearance properties of these glycopeptides, compared with the unlabeled native peptide, and these properties are highly favorable for positron emission tomography imaging. A high uptake of 18F-β-gluco-c(RGDfC) is shown by positron emission tomography imaging in a subcutaneous abscess model in the rat, revealing the potential of this tracer to monitor integrin expression as a part of inflammation and/or angiogenesis processes.

  这项工作描述了新型6-[18F]氟代碳水化合物衍生辅基的开发，这些辅基配备了一个叠氮臂，能够在温和条件下参与铜(I)催化的环加成反应，用于生物分子18F标记。本文介绍了这些不同辅基的高放射化学产率（最高达68 ± 6%）的放射性标记。将叠氮臂引入到碳水化合物部分所提供的灵活性，使得其能与不同的炔基功能化肽（如谷胱甘肽或精氨酸-甘氨酸-天冬氨酸衍生物）高效进行点击反应，从而制备糖肽。18F标记糖肽的放射合成在自动化过程中以高放射化学产率（高达76%）进行，并且具有优异的放射性化学纯度。与未标记的天然肽相比，在肽上附加糖部分应改善这些糖肽的生物利用度、药代动力学和体内清除特性，这些特性对于正电子发射断层扫描成像非常有利。正电子发射断层扫描成像显示，18F-β-葡糖-c(RGDfC)在大鼠皮下脓肿模型中具有高摄取量，揭示了这种示踪剂在监测作为炎症和/或血管生成过程一部分的整合素表达方面的潜力。
• Carbohydrate Microarrays for Assaying Galactosyltransferase Activity
  作者：Sungjin Park、Injae Shin

  DOI：10.1021/ol070250l

  日期：2007.4.1

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.
• DERIVES DE GLYCOSIDES, LEUR PREPARATION ET LEUR UTILISATION COMME GROUPES PROSTHETIQUES
  申请人：Université de Lorraine

  公开号：EP2867244A1

  公开（公告）日：2015-05-06