N-succinyl-3β-amino-5-cholestene | 334700-85-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: N-succinyl-3β-amino-5-cholestene
• 英文别名: 4-[[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]amino]-4-oxobutanoic acid
• CAS: 334700-85-5
• 化学式: C₃₁H₅₁NO₃
• 分子量: 485.751
• InChiKey: FGXSZCDYQUDZHH-MIXBDBMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-succinyl-3β-amino-5-cholestene 在 N-甲基吗啉 、 盐酸 、 N-羟基-7-氮杂苯并三氮唑 、 碳酸氢钠 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 3β-amino-5-cholestene-N,N-succinyl-2-N-aminoethyl[4-deoxy-4-N-(2-iodoacetyl)glycylglucopyranosyl]-(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
• 作为产物：
  描述：

  (3b)-胆甾-5-烯-3-胺 在 甲酸 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 N-succinyl-3β-amino-5-cholestene
  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

文献信息

• Derivatization of a Bioorthogonal Protected Trisaccharide Linker—Toward Multimodal Tools for Chemical Biology
  作者：Timmy Fyrner、Karin Magnusson、K. Peter R. Nilsson、Per Hammarström、Daniel Aili、Peter Konradsson

  DOI：10.1021/bc300160a

  日期：2012.6.20

  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.