Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester | 180154-26-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
• 英文别名: [(2R,3S,4S,5R,6S)-6-[(2R,3S,4R,5R,6R)-5-acetamido-4-(2-hydroxyethoxy)-2-(phenylmethoxymethyl)-6-propoxyoxan-3-yl]oxy-3,4,5-triacetyloxyoxan-2-yl]methyl acetate
• CAS: 180154-26-1
• 化学式: C₃₄H₄₉NO₁₆
• 分子量: 727.76
• InChiKey: BBGDVBPSLTVTAG-IUTRMQRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  51
• 可旋转键数：
  22
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  210
• 氢给体数：
  2
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 在 sodium methylate 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 27.5h， 生成 C₆₁H₇₈N₂O₁₅
  参考文献：
  名称：

  Synergistic Inhibition of Human α-1,3-Fucosyltransferase V

  摘要：

  Human alpha-1,3-fucosyltransferase V (FucT V), which catalyzes the transfer of L-fucose moiety from guanosine diphosphate beta-L-fucose (GDP-Fuc) to an acceptor sugar To form sialyl Lewis x (sLe(x)), was shown to proceed through an ordered, sequential mechanism by product inhibition studies. The designed azatrisaccharide propyl 2-acetamido-2-deoxy-4-O-(beta-D-galactopyranosyl)-3 -O-(2-(N-(beta-L-homofuconojirimycinyl))ethyl)-alpha-D- glucopyranoside (2), prepared by covalently linking the N-group of beta-L-homofuconojirimycin (1) to the 3-OH of LacNAc through an ethylene unit, in the presence of GDP was found to be an effective inhibitor of FucT V. In the presence of 30 mu M GDP, the concentration of 2 necessary to cause 50% inhibition was reduced 77-fold to 31 mu M. Presumably, the azatrisaccharide and GDP form a complex which mimics the transition state of the enzymatic reaction. Given the low affinity of FucT V for its substrate LacNAc (K-m = 35 mM), the designed azatrisaccharide in the presence of GDP represents the most potent synergistic inhibitor complex reported so far.

  DOI：

  10.1021/ja960274f
• 作为产物：
  描述：

  Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-oxo-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 0.33h， 生成 Acetic acid (2S,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6R)-5-acetylamino-2-benzyloxymethyl-4-(2-hydroxy-ethoxy)-6-propoxy-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Synergistic Inhibition of Human α-1,3-Fucosyltransferase V

  摘要：

  Human alpha-1,3-fucosyltransferase V (FucT V), which catalyzes the transfer of L-fucose moiety from guanosine diphosphate beta-L-fucose (GDP-Fuc) to an acceptor sugar To form sialyl Lewis x (sLe(x)), was shown to proceed through an ordered, sequential mechanism by product inhibition studies. The designed azatrisaccharide propyl 2-acetamido-2-deoxy-4-O-(beta-D-galactopyranosyl)-3 -O-(2-(N-(beta-L-homofuconojirimycinyl))ethyl)-alpha-D- glucopyranoside (2), prepared by covalently linking the N-group of beta-L-homofuconojirimycin (1) to the 3-OH of LacNAc through an ethylene unit, in the presence of GDP was found to be an effective inhibitor of FucT V. In the presence of 30 mu M GDP, the concentration of 2 necessary to cause 50% inhibition was reduced 77-fold to 31 mu M. Presumably, the azatrisaccharide and GDP form a complex which mimics the transition state of the enzymatic reaction. Given the low affinity of FucT V for its substrate LacNAc (K-m = 35 mM), the designed azatrisaccharide in the presence of GDP represents the most potent synergistic inhibitor complex reported so far.

  DOI：

  10.1021/ja960274f