N-(3-acetylthiopropanoyl)-2-aminoethyl (4-deoxy-4-N-tert-butyloxycarbonylglycylglucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside | 1381880-18-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(3-acetylthiopropanoyl)-2-aminoethyl (4-deoxy-4-N-tert-butyloxycarbonylglycylglucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside
• CAS: 1381880-18-7
• 化学式: C₃₂H₅₅N₃O₂₀S
• 分子量: 833.863
• InChiKey: RPQMQRINMKNEIP-BZNGUAJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.11
• 重原子数：
  56.0
• 可旋转键数：
  17.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  351.05
• 氢给体数：
  12.0
• 氢受体数：
  21.0

反应信息

• 作为反应物：
  描述：

  N-(3-acetylthiopropanoyl)-2-aminoethyl (4-deoxy-4-N-tert-butyloxycarbonylglycylglucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 在 盐酸 、 sodium methylate 作用下， 以 甲醇 、 水 为溶剂， 反应 2.5h， 生成 N-(3-thiopropanoyl)-2-aminoethyl (4-deoxy-4-N-glycylglucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranosylammonium hydrochloride
  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
• 作为产物：
  描述：

  2-(N-benzyloxycarbonyl)-aminoethyl (4-deoxy-4-N-tert-butyloxycarbonyl-glycyl-β-D-glucopyranosyl)-(1->3)-(β-D-galactopyranosyl)-(1->4)-β-D-glucopyranoside 在 palladium 10% on activated carbon 、 氢气 、 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 生成 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