1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranose | 98293-07-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranose
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-5-(1,3-dioxoisoindol-2-yl)-6-[(2R,3S,4S,5R,6R)-2,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 98293-07-3
• 化学式: C₃₄H₃₉NO₁₉
• 分子量: 765.679
• InChiKey: GUHSOAMBRWWBJU-QKKFVUIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  54
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  249
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranose 在 氢溴酸 作用下， 以 氯仿 、 溶剂黄146 为溶剂， 反应 12.0h， 以82.5%的产率得到3,4,6-tri-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranosyl bromide
  参考文献：
  名称：

  Takeda, Tadahiro; Fujisawa, Shin-ichi; Ogihara, Yukio, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 2, p. 540 - 543

  摘要：

  DOI：
• 作为产物：
  描述：

  (2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol 在 2,4,6-三甲基吡啶 、 硫酸 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 乙酸酐 为溶剂， 反应 15.0h， 生成 1,3,4,6-tetra-O-acetyl-2-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-D-mannopyranose
  参考文献：
  名称：

  Takeda, Tadahiro; Fujisawa, Shin-ichi; Ogihara, Yukio, Chemical and pharmaceutical bulletin, 1985, vol. 33, # 2, p. 540 - 543

  摘要：

  DOI：

文献信息

• Synthesis of a truncated bi-antennary complex-type N-glycan oxazoline; glycosylation catalysed by the endohexosaminidases Endo A and Endo M
  作者：Thomas B. Parsons、James W. B. Moir、Antony J. Fairbanks

  DOI：10.1039/b907273j

  日期：——

  The synthesis of a truncated complex N-glycan hexasaccharide oxazoline was achieved producing a substrate that was assayed as an activated donor for glycosylation catalysed by the endohexosaminidases Endo A and Endo M. For Endo M competitive product hydrolysis was seen to limit synthetic efficiency. In spite of its natural hydrolytic selectivity wild type Endo A was able to process the truncated complex N-glycan oxazoline, albeit with limited synthetic efficiency; notably the product was not a substrate for Endo A catalysed hydrolysis. Two Endo A mutants, E173Q and E173H, were also assayed, but were unable to process this oxazoline.

  我们成功合成了一种截断的复杂N-糖苷六糖苷酸的噁唑啉，并将其作为底物进行评估，以用作由内糖胺酶Endo A和Endo M催化的糖基化反应的活化供体。对于Endo M，竞争性产物水解被观察到限制了合成效率。尽管天然的水解选择性较高，野生型Endo A仍能够处理这种截断的复杂N-糖苷噁唑啉，但合成效率有限；值得注意的是，所生成的产物并不是Endo A催化水解的底物。同时评估了两个Endo A突变体，E173Q和E173H，但它们无法处理该噁唑啉。