2-azidoethyl 2-amino-2-deoxy-β-D-glucopyranoside | 804557-74-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-azidoethyl 2-amino-2-deoxy-β-D-glucopyranoside
• 英文别名: (2R,3S,4R,5R,6R)-5-amino-6-(2-azidoethoxy)-2-(hydroxymethyl)oxane-3,4-diol
• CAS: 804557-74-2
• 化学式: C₈H₁₆N₄O₅
• 分子量: 248.239
• InChiKey: PVIHBPRBQXAAPY-FMDGEEDCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 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：
  120
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-azidoethyl 2-amino-2-deoxy-β-D-glucopyranoside 在 甲醇 、 sodium methylate 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  A Chemoenzymatic Approach to Glycopeptide Antibiotics

  摘要：

  Many biologically active natural products are constrained by macrocyclization and modified with carbohydrates. These two types of modifications are essential for their biological activities. Here we report a chemoenzymatic approach to make carbohydrate-modified cyclic peptide antibiotics. Using a thioesterase domain from the decapeptide tyrocidine synthetase, 13 head-to-tail cyclized tyrocidine derivatives were obtained with one to three propargylglycines incorporated at positions 3-8. These cyclic peptides were then conjugated to 21 azido sugars via copper(I)-catalyzed cycloaddition. Antibacterial and hemolytic assays showed that the two best glycopeptides, Tyc4PG-14 and Tyc4PG-15, have a 6-fold better therapeutic index than the natural tyrocidine. We believe this method will also be useful for modifying other natural products to search for new therapeutics.

  DOI：

  10.1021/ja045147v
• 作为产物：
  描述：

  2'-azidoethyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 hydrazine hydrate 作用下， 以 乙醇 为溶剂， 反应 0.5h， 生成 2-azidoethyl 2-amino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  活体小鼠体内引发的原位聚合还原

  摘要：

  对生理或生化刺激作出反应的“智能”生物材料已在组织工程、治疗学和分子成像方面有许多生物医学应用。在这项工作中，我们描述了可激活双正交小分子的原位聚合，以响应减少体内环境变化。我们设计了一种基于碳水化合物连接体和氰基苯并噻唑-半胱氨酸缩合反应的小分子支架，它可以在物理化学变化（例如还原环境）下发生快速缩合反应，形成聚合物（拟多糖）。采用双模态光学成像方法检查了转化前后荧光团标记的缩合支架的荧光和光声特性。这些结果证实了该探针在活体小鼠局部和全身给药后的原位聚合。

  DOI：

  10.1021/jacs.0c07594

文献信息

• Synthesis and application of clickable and biocompatible fluorescent glycosyl labels
  作者：Zhiwei Lei、Jie Wang、Yuxin Tian、Gaopeng Song、Gang Zhao、Hanhong Xu

  DOI：10.1016/j.dyepig.2014.09.037

  日期：2015.2

  Two novel, biocompatible and highly stereoselective fluorescent glycosyl labels featuring azide groups have been successfully synthesized. The functional groups provide convenient routes for fluorescent glycosyl conjugates via click chemistry. Three fluorescent glycose-conjugates were synthesized. One fluorescent conjugate was used to trace the translocation in castor seedlings. The developed fluorescent labels for biomolecules are likely to provide an important method for investigating various biological events. We believe that the probes obtained are useful for studies on biological processes. (C) 2014 Elsevier Ltd. All rights reserved.
• A Chemoenzymatic Approach to Glycopeptide Antibiotics
  作者：Hening Lin、Christopher T. Walsh

  DOI：10.1021/ja045147v

  日期：2004.11.1

  Many biologically active natural products are constrained by macrocyclization and modified with carbohydrates. These two types of modifications are essential for their biological activities. Here we report a chemoenzymatic approach to make carbohydrate-modified cyclic peptide antibiotics. Using a thioesterase domain from the decapeptide tyrocidine synthetase, 13 head-to-tail cyclized tyrocidine derivatives were obtained with one to three propargylglycines incorporated at positions 3-8. These cyclic peptides were then conjugated to 21 azido sugars via copper(I)-catalyzed cycloaddition. Antibacterial and hemolytic assays showed that the two best glycopeptides, Tyc4PG-14 and Tyc4PG-15, have a 6-fold better therapeutic index than the natural tyrocidine. We believe this method will also be useful for modifying other natural products to search for new therapeutics.
• Reduction Triggered <i>In Situ</i> Polymerization in Living Mice
  作者：Lina Cui、Sandro Vivona、Bryan Ronain Smith、Sri-Rajasekhar Kothapalli、Jun Liu、Xiaowei Ma、Zixin Chen、Madelynn Taylor、Paul H. Kierstead、Jean M.J. Fréchet、Sanjiv S. Gambhir、Jianghong Rao

  DOI：10.1021/jacs.0c07594

  日期：2020.9.9

  responsive to physiological or biochemical stimuli have found many biomedical applications for tissue engineering, therapeutics and molecular imaging. In this work we describe in situ polymerization of activatable biorthogonal small molecules in response to reducing environment change in vivo. We designed a carbohydrate linker- and cyanobenzothiazole-cysteine condensation reaction-based small molecule scaffold

  对生理或生化刺激作出反应的“智能”生物材料已在组织工程、治疗学和分子成像方面有许多生物医学应用。在这项工作中，我们描述了可激活双正交小分子的原位聚合，以响应减少体内环境变化。我们设计了一种基于碳水化合物连接体和氰基苯并噻唑-半胱氨酸缩合反应的小分子支架，它可以在物理化学变化（例如还原环境）下发生快速缩合反应，形成聚合物（拟多糖）。采用双模态光学成像方法检查了转化前后荧光团标记的缩合支架的荧光和光声特性。这些结果证实了该探针在活体小鼠局部和全身给药后的原位聚合。