N4-β-D-glucopyranosyl-D-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)]-[β-D-mannopyranosyl-(1->4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-N2-(benzyloxycarbonyl)-L-asparagine methyl ester | 1186583-30-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N4-β-D-glucopyranosyl-D-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)]-[β-D-mannopyranosyl-(1->4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-N2-(benzyloxycarbonyl)-L-asparagine methyl ester
• 英文别名: N4-β-D-glucopyranosyl-D-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)]-β-D-mannopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-1-methyl-N2-(benzyloxycarbonyl)-L-asparagine；methyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3S,4S,5R,6R)-4-[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-[[(2S,3S,4S,5S,6R)-3-[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-4-oxo-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 1186583-30-1
• 化学式: C₆₃H₉₈N₆O₄₀
• 分子量: 1579.49
• InChiKey: IMMJEUSJCCZTGC-RIPWWWMYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -12.7
• 重原子数：
  109
• 可旋转键数：
  32
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  694
• 氢给体数：
  24
• 氢受体数：
  40

反应信息

• 作为产物：
  描述：

  Nα-(benzyloxycarbonyl)-Nγ-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-L-asparagine O-methyl ester 、 GlcNAc2Man3-ox 在 wild-type Endo M enzyme 作用下， 以 水 为溶剂， 反应 1.17h， 以22%的产率得到N4-β-D-glucopyranosyl-D-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->6)-[2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->2)-α-D-mannopyranosyl-(1->3)]-[β-D-mannopyranosyl-(1->4)]-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-N2-(benzyloxycarbonyl)-L-asparagine methyl ester
  参考文献：
  名称：

  Synthesis of a truncated bi-antennary complex-type N-glycan oxazoline; glycosylation catalysed by the endohexosaminidases Endo A and Endo M

  摘要：

  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。

  DOI：

  10.1039/b907273j

文献信息

• Streptococcus pneumoniae endohexosaminidase D; feasibility of using N-glycan oxazoline donors for synthetic glycosylation of a GlcNAc-asparagine acceptor
  作者：Thomas B. Parsons、Mitul K. Patel、Alisdair B. Boraston、David J. Vocadlo、Antony J. Fairbanks

  DOI：10.1039/b926078a

  日期：——

  Endohexosaminidase D, a family 85 glycoside hydrolase from S. pneumoniae and the first endohexosaminidase to be discovered, is found to be capable of catalysing the glycosylation of a glycosyl amino acid bearing a GlcNAc residue using a variety of N-glycan oxazoline donors. Although enzyme-catalysed oxazoline hydrolysis is a significant competing reaction that is not countered by the addition of organic

  内切葡糖胺酶D是来自肺炎链球菌的85家族糖苷水解酶，并且是发现的第一个内切葡糖胺酶，能够使用多种N-聚糖恶唑啉供体催化带有GlcNAc残基的糖基氨基酸的糖基化。虽然是酶催化的恶唑啉 水解是一种重要的竞争性反应，不能通过添加有机助溶剂或改变反应pH来抵消，可以通过依次添加多当量的有机溶剂来实现高收率的合成工艺 恶唑啉供体，证明了该酶作为合成确定的糖缀合物的生物催化剂的合成潜力。值得注意的是，Endo-D在所用条件下似乎不水解所得产物。远藤D展示的合成活性表明，其他未经测试的家族GH85酶可能显示出相似的合成潜力。此外，由于Endo D能够裂解连接到单克隆抗体（mAbs）的N-聚糖，并且还能够裂解被核心岩藻糖基化的聚糖，因此Endo D作为有用的生物催化剂的发展，可能用于合成重要的定义均质复合糖缀合物未来的巨大潜力，但前提是直接恶唑啉 可以克服水解作用。
• 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。