5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[(2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoyl)amino]ethyl]pentanamide | 1238077-44-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 生物素及其衍生物
• 英文名称: 5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[(2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoyl)amino]ethyl]pentanamide
• CAS: 1238077-44-5
• 化学式: C₂₉H₅₂N₄O₃S₄
• 分子量: 633.021
• InChiKey: VJFZXPPTTAVBCH-LSQMVHIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.6
• 重原子数：
  40
• 可旋转键数：
  23
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  207
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  S-dodecyl-S'-(α,α-dimethylpentafluorophenyl acetate)trithiocarbonate 、 (3aS,4S,6aR)-N-(2-氨基乙基)六氢-2-氧代-1H-噻吩并[3,4-d]咪唑-4-戊酰胺 以 N,N-二甲基甲酰胺 为溶剂， 以45.4 mg的产率得到5-[(3aS,4S,6aR)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-N-[2-[(2-dodecylsulfanylcarbothioylsulfanyl-2-methylpropanoyl)amino]ethyl]pentanamide
  参考文献：
  名称：

  Synthesis of Glycopolymers for Microarray Applications via Ligation of Reducing Sugars to a Poly(acryloyl hydrazide) Scaffold

  摘要：

  In this paper, we report on a general synthetic strategy for the assembly of glycopolymers that capitalizes on the intrinsic reactivity of reducing glycans toward hydrazides to form stable cyclic N-glycosides. We developed a poly(acryloyl hydrazide) (PAH) scaffold to which we conjugated a variety of reducing glycans ranging in structure from simple mono- and disaccharides to considerably more complex human milk and blood oligosaccharides. The conjugation proceeds under mild conditions with excellent ligation efficiencies and in a stereoselective manner, providing glycopolymers with pendant glycans accommodated mostly in their cyclic beta-glycosidic form. Utilizing a biotin-terminated PAH scaffold prepared via RAFT polymerization, we quickly assembled a panel of glycopolymers that we microarrayed on streptavidin-coated glass. We then demonstrated that in these microarrays, the glycopolymer ligands bind lectins according to the structures of their pendant glycans. Importantly, glycopolymers containing biologically relevant branched oligosaccharides, such as sialyl Lewis(x), as well as sulfated glycosaminoglycan-like epitopes can be readily prepared using our methodology.

  DOI：

  10.1021/ja103009d

文献信息

• Synthesis of Glycopolymers for Microarray Applications via Ligation of Reducing Sugars to a Poly(acryloyl hydrazide) Scaffold
  作者：Kamil Godula、Carolyn R. Bertozzi

  DOI：10.1021/ja103009d

  日期：2010.7.28

  In this paper, we report on a general synthetic strategy for the assembly of glycopolymers that capitalizes on the intrinsic reactivity of reducing glycans toward hydrazides to form stable cyclic N-glycosides. We developed a poly(acryloyl hydrazide) (PAH) scaffold to which we conjugated a variety of reducing glycans ranging in structure from simple mono- and disaccharides to considerably more complex human milk and blood oligosaccharides. The conjugation proceeds under mild conditions with excellent ligation efficiencies and in a stereoselective manner, providing glycopolymers with pendant glycans accommodated mostly in their cyclic beta-glycosidic form. Utilizing a biotin-terminated PAH scaffold prepared via RAFT polymerization, we quickly assembled a panel of glycopolymers that we microarrayed on streptavidin-coated glass. We then demonstrated that in these microarrays, the glycopolymer ligands bind lectins according to the structures of their pendant glycans. Importantly, glycopolymers containing biologically relevant branched oligosaccharides, such as sialyl Lewis(x), as well as sulfated glycosaminoglycan-like epitopes can be readily prepared using our methodology.