O-(2,3,4-Tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)>-2-acetamido-1,6-anhydro-2-deoxy-β-D-glucopyranose | 162710-72-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: O-(2,3,4-Tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)>-2-acetamido-1,6-anhydro-2-deoxy-β-D-glucopyranose
• 英文别名: [(2R,3R,4R,5R,6R)-5-acetamido-6-[(2S,3R,4S,5S,6R)-2-[[(1R,2S,3R,4R,5R)-4-acetamido-3-[(2S,3S,4R,5R,6S)-3,4,5-triacetyloxy-6-methyloxan-2-yl]oxy-6,8-dioxabicyclo[3.2.1]octan-2-yl]oxy]-3,5-diacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxy-3,4-diacetyloxyoxan-2-yl]methyl acetate
• CAS: 162710-72-7
• 化学式: C₄₆H₆₄N₂O₂₈
• 分子量: 1093.01
• InChiKey: CWINHNQNSBTLQI-LXGWHGOZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  76
• 可旋转键数：
  28
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  369
• 氢给体数：
  2
• 氢受体数：
  28

反应信息

• 作为反应物：
  描述：

  O-(2,3,4-Tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)>-2-acetamido-1,6-anhydro-2-deoxy-β-D-glucopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以92%的产率得到O-(α-L-Fucopyranosyl)-(1->3)-3)-O-(β-D-galactopyranosyl)-(1->4)>-2-acetamido-1,6-anhydro-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharides Structurally Related to E-Selectin Ligands Are Inhibitors of Neural Cell Division: Synthesis, Conformational Analysis, and Biological Activity

  摘要：

  Oligosaccharides containing either the Lewis X trisaccharide fragment (3-fucosyl-N-acetyllactosamine) with N-acetylgalactosamine at the C-3 position of the galactose unit (compound 2 and the 1,6-anhydro derivative 5) or the trisaccharide 3-fucosyllactose having N-acetylneuraminic and sulfate groups at the C-3; position of the galactose (3 and 4, respectively) have been synthesized and tested for the ability to inhibit the division of astrocytes and transformed cell lines and their conformation studied. Compounds 3 and Care structurally related to sulfated Lewis X and sialyl Lewis X which are known to be recognized by E-selectin. The synthesis of 2 and 5 was accomplished by an original route starting from 1,6-anhydro-beta-D-mannose, while 3 and 4 were efficiently prepared from methyl beta-lactoside. The conformational analysis has been carried out using NMR, molecular mechanics, and molecular dynamics. Compounds 2-4 were inhibitors in all cell types tested showing ID50 values in the mu M range; however, 5 showed a marked decrease in the ID50 value on astrocytes emphasizing upon the importance of the relative orientation of the fucosyl unit. Tetrasaccharide 3 was the most active on astrocytes (ID50 = 35 mu M), whereas the sulfate 4 was the best inhibitor on tumor-forming C6 glioma cells (ID50 = 79 mu M).

  DOI：

  10.1021/jo00111a008
• 作为产物：
  描述：

  乙酸酐 、 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 生成 O-(2,3,4-Tri-O-acetyl-α-L-fucopyranosyl)-(1->3)-3)-O-(2,4,6-tri-O-acetyl-β-D-galactopyranosyl)-(1->4)>-2-acetamido-1,6-anhydro-2-deoxy-β-D-glucopyranose
  参考文献：
  名称：

  Oligosaccharides Structurally Related to E-Selectin Ligands Are Inhibitors of Neural Cell Division: Synthesis, Conformational Analysis, and Biological Activity

  摘要：

  Oligosaccharides containing either the Lewis X trisaccharide fragment (3-fucosyl-N-acetyllactosamine) with N-acetylgalactosamine at the C-3 position of the galactose unit (compound 2 and the 1,6-anhydro derivative 5) or the trisaccharide 3-fucosyllactose having N-acetylneuraminic and sulfate groups at the C-3; position of the galactose (3 and 4, respectively) have been synthesized and tested for the ability to inhibit the division of astrocytes and transformed cell lines and their conformation studied. Compounds 3 and Care structurally related to sulfated Lewis X and sialyl Lewis X which are known to be recognized by E-selectin. The synthesis of 2 and 5 was accomplished by an original route starting from 1,6-anhydro-beta-D-mannose, while 3 and 4 were efficiently prepared from methyl beta-lactoside. The conformational analysis has been carried out using NMR, molecular mechanics, and molecular dynamics. Compounds 2-4 were inhibitors in all cell types tested showing ID50 values in the mu M range; however, 5 showed a marked decrease in the ID50 value on astrocytes emphasizing upon the importance of the relative orientation of the fucosyl unit. Tetrasaccharide 3 was the most active on astrocytes (ID50 = 35 mu M), whereas the sulfate 4 was the best inhibitor on tumor-forming C6 glioma cells (ID50 = 79 mu M).

  DOI：

  10.1021/jo00111a008