2-bromoethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside | 254903-98-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-bromoethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
• 英文别名: 2-bromoethyl α-D-glucopyranoside；2-bromoethyl-α-D-glucopyranoside；(2-bromoethyl)-α-D-glucoside；1-α-bromoethyl-glucose；(2S,3R,4S,5S,6R)-2-(2-bromoethoxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 254903-98-5
• 化学式: C₈H₁₅BrO₆
• 分子量: 287.107
• InChiKey: BQGLYRBERUCSMN-CBQIKETKSA-N

物化性质

• 沸点：
  479.0±45.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-bromoethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 sodium azide 、 sodium iodide 作用下， 以 水 为溶剂， 生成 azidoethylglucose
  参考文献：
  名称：

  DRUG-LIGAND CONJUGATES, SYNTHESIS THEREOF, AND INTERMEDIATES THERETO

  摘要：

  本发明涉及一种合成式I化合物或其药用可接受盐的方法：（I），其中X、Alk和W中的每一个如本文所定义和描述。

  公开号：

  US20130131310A1
• 作为产物：
  描述：

  2'-bromoethyl-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以94%的产率得到2-bromoethyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside
  参考文献：
  名称：

  Controlled Site-Selective Glycosylation of Proteins by a Combined Site-Directed Mutagenesis and Chemical Modification Approach

  摘要：

  DOI：

  10.1021/jo9816461

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。
• Preparation and mass-spectral analysis of O-hydroxy-ethyl derivatives of d-glucose
  作者：Katsuyuki Nagai、Atsuko Honda、Tadashi Kiho、Shigeo Ukai、Teruo Tsuchiya

  DOI：10.1016/0008-6215(89)84123-0

  日期：1989.7

  Various hydroxyethyl ethers of d-glucose have been prepared in good yield by treating d-glucose derivatives with 2-bromoethyl tetrahydropyranyl ether in the presence of sodium hydride. The derived O-(hydroxyethyl)-d-glucitol acetates exhibited characteristic mass-spectral fragments. The furanose and pyranose forms of 1,2-O-ethylene-d-glucose derived from 2-O-(2-hydroxyethyl)-d-glucose were identified

  通过在氢化钠存在下用2-溴乙基四氢吡喃基醚处理d-葡萄糖衍生物，以高收率制备了各种d-葡萄糖的羟乙基醚。衍生的O-（羟乙基）-d-葡萄糖醇乙酸酯表现出特征的质谱碎片。通过质谱分析鉴定了衍生自2-O-（2-羟乙基）-d-葡萄糖的1,2-O-乙烯-d-葡萄糖的呋喃糖和吡喃糖形式。
• ‘Click’ glycosylation of peptides through cysteine propargylation and CuAAC
  作者：Sandrine Lamandé-Langle、Charlotte Collet、Raphaël Hensienne、Christine Vala、Françoise Chrétien、Yves Chapleur、Amel Mohamadi、Patrick Lacolley、Véronique Regnault

  DOI：10.1016/j.bmc.2014.09.056

  日期：2014.12

  'Click' glycosylation of cysteine-containing peptides were carried out in good yield by Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC). For that peptides were functionalized though direct propargylation of the cysteine residue allowing their use in CuAAC with suitable free or protected azido sugars of gluco, manno and galacto configuration. Among these free and protected glycopeptides a series of 'glycoRGD' peptides were obtained and submitted to in vitro platelet aggregation tests, showing that the pseudoglycosylation of the adhesion sequence lowers the IC50 value and thus could improve the in vivo pharmacokinetic properties. (C) 2014 Elsevier Ltd. All rights reserved.

  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。
• Chemoselective Installation of Amine Bonds on Proteins through Aza-Michael Ligation
  作者：Allyson M. Freedy、Maria J. Matos、Omar Boutureira、Francisco Corzana、Ana Guerreiro、Padma Akkapeddi、Víctor J. Somovilla、Tiago Rodrigues、Karl Nicholls、Bangwen Xie、Gonzalo Jiménez-Osés、Kevin M. Brindle、André A. Neves、Gonçalo J. L. Bernardes

  DOI：10.1021/jacs.7b10702

  日期：2017.12.20

  method is demonstrated for three proteins and is shown to be fully compatible with disulfide bridges, as evidenced by the selective modification of recombinant albumin that displays 17 structurally relevant disulfides. The practicability and utility of our approach is further demonstrated by the construction of a chemically modified C2A domain of Synaptotagmin-I protein that retains its ability to preferentially

  蛋白质的化学修饰对于各种重要的诊断和治疗应用至关重要。迄今为止开发的许多策略缺乏化学和区域选择性，并导致非天然连接可能在体内不稳定并对蛋白质的结构和功能产生不利影响。我们在这里描述了 N-亲核试剂在蛋白质上下文中与氨基酸脱氢丙氨酸 (Dha) 的反应。当 Dha 以化学方式安装在蛋白质中时，添加范围广泛的 N-亲核试剂能够在温和的生物相容性条件下以化学选择性的方式快速形成胺键（二级和三级）。这些新的键在很宽的 pH 值范围（pH 2.8 至 12.8）、还原条件（生物硫醇，如谷胱甘肽）和人血浆中都是稳定的。这种方法对三种蛋白质进行了证明，并显示出与二硫键完全兼容，如重组白蛋白的选择性修饰所证明的那样，显示 17 种结构相关的二硫键。我们的方法的实用性和实用性通过构建 Synaptotagmin-I 蛋白的化学修饰 C2A 结构域得到进一步证明，该结构域保留其优先结合凋亡细胞的能力，其水平与
• Fluorescent dye-labeled glucose bioprobe, synthesis method and usage thereof
  申请人：Park Seung Bum

  公开号：US08772463B2

  公开（公告）日：2014-07-08

  Disclosed are a novel fluorescent glucose analogue, a method for the synthesis thereof and the use thereof. The novel fluorescent glucose analogue is labeled with fluorescent dye by O-1-glycosylation and via various linkers. The fluorescent glucose analogue can be applied to molecular bioimaging and a method for screening curative or preventive drugs for glucose metabolism-related diseases.

  本发明涉及一种新型荧光葡萄糖类似物，其合成方法和使用方法。该新型荧光葡萄糖类似物通过O-1-糖基化和各种连接剂标记荧光染料。该荧光葡萄糖类似物可用于分子生物成像以及筛选治疗或预防葡萄糖代谢相关疾病的药物的方法。