allyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-β-D-glucopyranoside | 934363-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-β-D-glucopyranoside
• 英文别名: N-[(2R,3R,4R,5S,6R)-5-[(2S,3R,4R,5S,6R)-3-azido-5-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-prop-2-enoxyoxan-3-yl]acetamide
• CAS: 934363-13-0
• 化学式: C₂₉H₄₈N₄O₂₀
• 分子量: 772.715
• InChiKey: FBCFEWAPQVKDIM-IGJVTKCWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -6.3
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  340
• 氢给体数：
  12
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  allyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-β-D-glucopyranoside 、 乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 24.0h， 以75%的产率得到allyl O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->4)-(3,6-di-O-acetyl-2-azido-2-deoxy-β-D-glucopyranosyl)-(1->4)-(3,6-di-O-acetyl-2-acetamido-β-D-glucopyranoside)
  参考文献：
  名称：

  Unexpected regioselectivity of Humicola insolens Cel7B glycosynthase mutants

  摘要：

  Four Humicola insolens Ce17B glycoside hydrolase mutants have been evaluated for the coupling of lactosyl fluoride on O-allyl N-I-acetyl-2(II)-azido-beta-chitobioside. Double mutants Ce17B E197A H209A and Ce1713 E197A H209G preferentially catalyze the formation of a beta-(1 -> 4) linkage between the two disaccharides, while single mutant Cel7B E197A and triple mutant Cel7B E197A H209A A211T produce predominantly the beta-(1 -> 3)-linked tetrasaccharide. This result constitutes the first report of the modulation of the regioselectivity through site-directed mutagenesis for an endoglycosynthase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.12.017
• 作为产物：
  描述：

  2-acetamido-4-O-(2-amnio-2-deoxy-β-D-glucopyranosyl)-2-deoxy-D-glucopyranoside 在 Humicola insolens Cel₇B E₁₉₇A H₂₀₉A glycosynthase triflic azide 、 三乙胺 、 zinc(II) chloride 作用下， 以 甲醇 、 phosphate buffer 、 二氯甲烷 、 acetate buffer 、 水 为溶剂， 反应 16.5h， 生成 allyl O-β-D-galactopyranosyl-(1->4)-β-D-glucopyranosyl-(1->4)-2-azido-2-deoxy-β-D-glucopyranosyl-(1->4)-2-acetamido-β-D-glucopyranoside
  参考文献：
  名称：

  Unexpected regioselectivity of Humicola insolens Cel7B glycosynthase mutants

  摘要：

  Four Humicola insolens Ce17B glycoside hydrolase mutants have been evaluated for the coupling of lactosyl fluoride on O-allyl N-I-acetyl-2(II)-azido-beta-chitobioside. Double mutants Ce17B E197A H209A and Ce1713 E197A H209G preferentially catalyze the formation of a beta-(1 -> 4) linkage between the two disaccharides, while single mutant Cel7B E197A and triple mutant Cel7B E197A H209A A211T produce predominantly the beta-(1 -> 3)-linked tetrasaccharide. This result constitutes the first report of the modulation of the regioselectivity through site-directed mutagenesis for an endoglycosynthase. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2006.12.017