1-O-but-3-ynyl-α-D-galactopyranoside | 1190202-80-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-but-3-ynyl-α-D-galactopyranoside
• 英文别名: (2R,3R,4S,5R,6R)-2-(but-3-yn-1-yloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol；but-3-yn-1-yl β-D-galactopyranoside；3-butynyl galactopyranoside；(2R,3R,4S,5R,6R)-2-but-3-ynoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 1190202-80-2
• 化学式: C₁₀H₁₆O₆
• 分子量: 232.233
• InChiKey: LYCIVKHZSWRECA-SOYHJAILSA-N

物化性质

• 沸点：
  440.0±45.0 °C(Predicted)
• 密度：
  1.39±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  1-O-but-3-ynyl-α-D-galactopyranoside 在 吡啶 作用下， 反应 16.0h， 生成 (2R,3R,4S,5S,6R)-2-(but-3-yn-1-yloxy)-6-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-3,4,5-triyl tribenzoate
  参考文献：
  名称：

  [EN] HYPOIMMUNOGENIC BIOTHERAPEUTICS
  [FR] BIOTHÉRAPEUTIQUES HYPOIMMUNOGÈNES

  摘要：

  本公开提供了一种低免疫原性生物治疗组合物，可抑制个体对其产生免疫反应。本公开还提供了包含此类低免疫原性生物治疗剂的制药组合物，制备此类低免疫原性生物治疗剂的方法，以及将此类低免疫原性生物治疗剂用作治疗和研究的方法。

  公开号：

  WO2022150726A1
• 作为产物：
  描述：

  but-3-ynyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以93%的产率得到1-O-but-3-ynyl-α-D-galactopyranoside
  参考文献：
  名称：

  用于多价蛋白质支架工程的蛋白质正交双重修饰。

  摘要：

  为了向基于蛋白质的多价支架设计添加新工具，我们开发了一种新颖的蛋白质双标记策略，该策略将非天然氨基酸的残基特异性掺入与蛋白质 N 末端的化学氧化醛形成结合起来。我们的方法依赖于通过相互正交的铜催化叠氮-炔环加成（CuAAC）和肟连接在蛋白质中选择性引入两个不同的功能部分。该方法应用于生物素和 β 连接半乳糖残基的缀合，产生具有酶活性的嗜热脂肪酶，通过 SPR 结合研究揭示了其与刺桐凝集素的特异性结合。

  DOI：

  10.3762/bjoc.11.88

文献信息

• Expanding the application scope of glycosidases using click chemistry
  作者：Wen-Ya Lu、Xing-Wen Sun、Chen Zhu、Jian-He Xu、Guo-Qiang Lin

  DOI：10.1016/j.tet.2009.11.044

  日期：2010.1

  Glycosidase-mediated glycosylation of alkynyl alcohols and azide-containing alcohols was followed by a click reaction, affording various types of triazole glycosides. The activities of triazole glycosides detected in Subsequent bioassays show that this procedure is a feasible approach to the development of anti-fungal drugs. (C) 2009 Elsevier Ltd. All rights reserved.
• Multifunctional Surface Modification of Gold-Stabilized Nanoparticles by Bioorthogonal Reactions
  作者：Xiuru Li、Jun Guo、Jinkeng Asong、Margreet A. Wolfert、Geert-Jan Boons

  DOI：10.1021/ja2012164

  日期：2011.7.27

  Nanocarriers that combine multiple properties in an all-in-one system hold great promise for drug delivery. The absence of technology to assemble highly functionalized devices has, however, hindered progress in nanomedicine. To address this deficiency, we have chemically synthesized poly(ethylene oxide)-beta-poly(epsilon-caprolactone) (PEO-b-PCL) block polymers modified at the apolar PCL terminus with thioctic acid and at the polar PEO terminus with an acylhydrazide, amine, or azide moiety. The resulting block polymers were employed to prepare nanoparticles that have a gold core, an apolar polyester layer for drug loading, a polar PEO corona to provide biocompatibility, and three different types of surface reactive groups for surface functionalization. The acylhydrazide, amine, or azide moieties of the resulting nanoparticles could be reacted with high efficiencies with modules having a ketone, isocyanate, or active ester and alkyne function, respectively. To demonstrate proof of principle of the potential of multisurface functionalization, we prepared nanoparticles that have various combinations of an oligo-arginine peptide to facilitate cellular uptake, a histidine-rich peptide to escape from lysosomes, and an Alexa Fluor 488 tag for imaging purposes. It has been shown that uptake and subcellular localization of the nanoparticles can be controlled by multisurface modification. It is to be expected that the modular synthetic methodology provides unique opportunities to establish optimal configurations of nanocarriers for disease-specific drug delivery.