N-[(2S,3R,4R,5S,6R)-2-Aminooxy-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide | 502457-62-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-[(2S,3R,4R,5S,6R)-2-Aminooxy-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• 英文别名: Gal(b1-4)GlcNAc(b)-O-NH2；N-[(2S,3R,4R,5S,6R)-2-aminooxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 502457-62-7
• 化学式: C₁₄H₂₆N₂O₁₁
• 分子量: 398.367
• InChiKey: MMKDEIJEZGMUKO-RCBHQUQDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.4
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  213
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R,4R,5S,6R)-2-Aminooxy-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 、 alkaline earth salt of/the/ methylsulfuric acid 在 α-2,3-sialyltransferase 、 manganese(ll) chloride 、 alkaline phosphatase 作用下， 反应 48.0h， 以76%的产率得到NeuAc(a2-3)Gal(b1-4)GlcNAc(b)-O-NH2
  参考文献：
  名称：

  A Method for the Generation of Glycoprotein Mimetics

  摘要：

  A general method for preparing glycoprotein mimetics with defined glycan structure using the Z domain protein as an example is reported. An unnatural amino acid containing the keto group was site-specifically incorporated into a target protein, Z domain, in response to the amber nonsense codon with high translational fidelity and efficiency. An aminooxy saccharide derivative was then selectively coupled to this genetically encoded keto group. The resulting saccharide core was elaborated to a glycan complex with glycosyltransferases. Alternatively, aminooxy analogues of more complicated glycans were prepared and directly attached to the keto group. Homogeneous glycoprotein mimetics thus prepared should prove useful for the study of carbohydrate effects on glycoprotein structure and function. This method may also lead to the production of glycoprotein therapeutics from Escherichia coli.

  DOI：

  10.1021/ja029433n
• 作为产物：
  描述：

  O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)hydroxylamine 、 alkaline earth salt of/the/ methylsulfuric acid 在 β-1,4-galactosyltransferase 、 manganese(ll) chloride 、 alkaline phosphatase 作用下， 反应 48.0h， 以70%的产率得到N-[(2S,3R,4R,5S,6R)-2-Aminooxy-4-hydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide
  参考文献：
  名称：

  A Method for the Generation of Glycoprotein Mimetics

  摘要：

  A general method for preparing glycoprotein mimetics with defined glycan structure using the Z domain protein as an example is reported. An unnatural amino acid containing the keto group was site-specifically incorporated into a target protein, Z domain, in response to the amber nonsense codon with high translational fidelity and efficiency. An aminooxy saccharide derivative was then selectively coupled to this genetically encoded keto group. The resulting saccharide core was elaborated to a glycan complex with glycosyltransferases. Alternatively, aminooxy analogues of more complicated glycans were prepared and directly attached to the keto group. Homogeneous glycoprotein mimetics thus prepared should prove useful for the study of carbohydrate effects on glycoprotein structure and function. This method may also lead to the production of glycoprotein therapeutics from Escherichia coli.

  DOI：

  10.1021/ja029433n

文献信息

• A Method for the Generation of Glycoprotein Mimetics
  作者：Haitian Liu、Lei Wang、Ansgar Brock、Chi-Huey Wong、Peter G. Schultz

  DOI：10.1021/ja029433n

  日期：2003.2.19

  A general method for preparing glycoprotein mimetics with defined glycan structure using the Z domain protein as an example is reported. An unnatural amino acid containing the keto group was site-specifically incorporated into a target protein, Z domain, in response to the amber nonsense codon with high translational fidelity and efficiency. An aminooxy saccharide derivative was then selectively coupled to this genetically encoded keto group. The resulting saccharide core was elaborated to a glycan complex with glycosyltransferases. Alternatively, aminooxy analogues of more complicated glycans were prepared and directly attached to the keto group. Homogeneous glycoprotein mimetics thus prepared should prove useful for the study of carbohydrate effects on glycoprotein structure and function. This method may also lead to the production of glycoprotein therapeutics from Escherichia coli.