(4R,5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-2-oxolanone

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (4R,5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxy-2-oxolanone
• 英文别名: (4R,5R)-5-(1,2-dihydroxyethyl)-3,4-dihydroxyoxolan-2-one
• 化学式: C₆H₁₀O₆
• 分子量: 178.14
• InChiKey: SXZYCXMUPBBULW-FKEBYDFPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

文献信息

• GLYCOPROTEOMIC PROBES FOR FLUORESCENT IMAGING OF FUCOSYLATED GLYCANS IN VIVO
  申请人：Wong Chi-Huey

  公开号：US20110257376A1

  公开（公告）日：2011-10-20

  Methods are provided for labeling cellular glycans bearing azide groups via fluorescent labeling comprising Cu(I)-catalyzed [3+2] cycloaddition of a probe comprising alkynyl group. Generation of fluorescent probes from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2] cycloaddition of the alkyne group of the probe to an azido-modified sugar are provided. Incorporation of azido-containing fucose analog into glycoconjugates via the fucose salvage pathway are disclosed. Fluorescent visualization of fucosylated cells by flow cytometry of cells treated with 6-azidofucose labeled with click-activated fluorogenic probe or biotinylated alkyne is disclosed. Visualization of intracellular location of fucosylated glycoconjugates by fluorescence microscopy are disclosed.

  提供了一种通过荧光标记的方法来标记带有偶氮基团的细胞糖基，包括利用含炔基的探针进行铜(I)催化的[3+2]环加成。通过将非荧光前体4-乙炔基-N-乙基-1,8-萘酰亚胺经铜(I)催化的[3+2]环加成，将探针的炔基与偶氮修饰糖的偶氮基团结合生成荧光探针。通过富马醇拯救途径将含偶氮基的富马醇类似物纳入糖蛋白中。通过流式细胞术将经6-偶氮基富马醇标记的细胞与点击活化的荧光探针或生物素化炔烃处理，实现对富马基细胞的荧光可视化。通过荧光显微镜揭示富马基糖蛋白的胞内位置。
• Glycoproteomic probes for fluorescent imaging of fucosylated glycans in vivo
  申请人：Wong Chi-Huey

  公开号：US20080241856A1

  公开（公告）日：2008-10-02

  The disclosure provides a method of labeling of cellular glycans bearing azide groups via a fluorescent labeling technique based on Cu(I)-catalyzed [3+2]cycloaddition (click activation) of a probe comprising an alkynyl group. The method entails generating a fluorescent probe from a nonfluorescent precursor, 4-ethynyl-N-ethyl-1,8-naphthalimide, by Cu(I)-catalyzed [3+2]cycloaddition of the alkyne group of the probe with an azido-modified sugar. The disclosure further provides a method of incorporating an azido-containing fucose analog into glycoconjugates via the fucose salvage pathway. The disclosure provides a method of fluorescent visualization of fucosylated cells by flow cytometry when cells treated with 6-azidofucose are labeled with the click-activated fluorogenic probe or biotinylated alkyne. A method of visualizing the intracellular localization of fucosylated glycoconjugates by fluorescence microscopy is also disclosed.
• US7910319B2
  申请人：——

  公开号：US7910319B2

  公开（公告）日：2011-03-22
• US8329413B2
  申请人：——

  公开号：US8329413B2

  公开（公告）日：2012-12-11