Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester | 178450-89-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
• CAS: 178450-89-0
• 化学式: C₃₆H₄₂O₂₀
• 分子量: 794.717
• InChiKey: NUHIJECUCNQZPZ-FVUSEMRQSA-N

物化性质

• 沸点：
  801.3±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  56.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  251.23
• 氢给体数：
  0.0
• 氢受体数：
  20.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester 在 E_.coli K₁₂ sialic acid aldolase 、 N_.meningitidis CMP-Sia synthetase tPm₀₁₈₈Ph 、 sodium methylate 、 胞苷-5’-三磷酸 、 magnesium chloride 作用下， 以 甲醇 、 various solvents 为溶剂， 反应 12.0h， 生成 4-methylumbelliferyl O-(5-[(2-propynyloxy)carbonyl]amido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosylonic acid)-(2->3)-O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranoside
  参考文献：
  名称：

  A Multifunctional Pasteurella multocida Sialyltransferase:  A Powerful Tool for the Synthesis of Sialoside Libraries

  摘要：

  A multifunctional sialyltransferase has been cloned from Pasteurella multocida strain P-1059 and expressed in E. coli as a truncated C-terminal His6-tagged recombinant protein (tPm0188Ph). Biochemical studies indicate that the obtained protein is (1) an alpha2,3-sialyltransferase (main function), (2) an alpha2,6-sialyltransferase, (3) an alpha2,3-sialidase, and (4) an alpha2,3-trans-sialidase. The recombinant tPm0188Ph is a powerful tool in the synthesis of structurally diverse sialoside libraries due to its relaxed substrate specificity, high solubility, high expression level, and multifunctionality.

  DOI：

  10.1021/ja0561690
• 作为产物：
  描述：

  羟甲香豆素 、 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-lactosyl trichloroacetimidate 在 4 A molecular sieve 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以90%的产率得到Acetic acid (2S,3R,4S,5R,6R)-3-acetoxy-6-acetoxymethyl-2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-5-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  A Multifunctional Pasteurella multocida Sialyltransferase:  A Powerful Tool for the Synthesis of Sialoside Libraries

  摘要：

  A multifunctional sialyltransferase has been cloned from Pasteurella multocida strain P-1059 and expressed in E. coli as a truncated C-terminal His6-tagged recombinant protein (tPm0188Ph). Biochemical studies indicate that the obtained protein is (1) an alpha2,3-sialyltransferase (main function), (2) an alpha2,6-sialyltransferase, (3) an alpha2,3-sialidase, and (4) an alpha2,3-trans-sialidase. The recombinant tPm0188Ph is a powerful tool in the synthesis of structurally diverse sialoside libraries due to its relaxed substrate specificity, high solubility, high expression level, and multifunctionality.

  DOI：

  10.1021/ja0561690