3-acetylthiopropionic acid N-hydroxysuccinimide ester | 153086-79-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: 3-acetylthiopropionic acid N-hydroxysuccinimide ester
• 英文别名: S-[3-(2,5-Dioxo-1-pyrrolidinyl)-3-oxopropyl] ethanethioate；S-[3-(2,5-dioxopyrrolidin-1-yl)-3-oxopropyl] ethanethioate
• CAS: 153086-79-4
• 化学式: C₉H₁₁NO₄S
• 分子量: 229.257
• InChiKey: PXHKYCUKMLFSQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.33
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  71.52
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3-acetylthiopropionic acid N-hydroxysuccinimide ester 、 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 以0.1 g的产率得到N-(3-acetylthiopropanoyl)-2-aminoethyl (4-deoxy-4-N-tert-butyloxycarbonylglycylglucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  Derivatization of a Bioorthogonal Protected Trisaccharide Linker—Toward Multimodal Tools for Chemical Biology

  摘要：

  When cross-linking biomolecules to surfaces or to other biomolecules, the use of appropriate spacer molecules is of great importance. Mimicking the naturally occurring spacer molecules will give further insight into their role and function, possibly unveil important issues regarding the importance of the specificity of carbohydrate-based anchor moieties, in e.g., glycoproteins and glycosylphosphatidylinositols. Herein, we present the synthesis of a lactoside-based trisaccharide, potentially suitable as a heterobifunctional bioorthogonal linker molecule whereon valuable chemical handles have been conjugated. An amino-derivative having thiol functionality shows promise as novel SPR-surfaces. Furthermore, the trisaccharide has been conjugated to a cholesterol moiety in combination with a fluorophore which successfully assemble on the cell surface in lipid microdomains, possibly lipid-rafts. Finally, a Cu-I-catalyzed azide alkyne cycloaddition reaction (CuAAC) confirms the potential use of oligosaccharides as bioorthogonal linkers in chemical biology.

  DOI：

  10.1021/bc300160a