(2,3,6-tri-O-acetyl-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride | 493006-09-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,6-tri-O-acetyl-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-fluorooxan-3-yl]oxy-3-(oxan-2-yloxy)oxan-2-yl]methyl acetate
• CAS: 493006-09-0
• 化学式: C₂₉H₄₁FO₁₇
• 分子量: 680.633
• InChiKey: OTVNUSHSPBRMKZ-WMLUPSFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  47
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  204
• 氢给体数：
  0
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  (2,3,6-tri-O-acetyl-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以98%的产率得到(4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Chemoenzymatic Syntheses of Linear and Branched Hemithiomaltodextrins as Potential Inhibitors for Starch-Debranching Enzymes

  摘要：

  Oligosaccharides embodying the S-maltosyl-6-thiomaltosyl structure have been readily synthesised by using convergent chemoenzymatic approaches. The key steps for the preparation of these molecules involved: 1) transglycosylation reactions of maltosyl fluorides onto suitable acceptors catalysed by the bacterial transglycosylase, cyclodextrin glycosyltransferase (CGTase), and 2) the S(N)2-type displacement of a 6-halide from acetylated acceptors by activated 1-thioglycoses. The target molecules, which were obtained in good overall yields, proved to be useful for investigating substrate binding in the active sites of several enzymes that act upon the alpha-1,6-linkage of pullulan and/or amylopectin. The compounds exhibit K-i values in the 2.5-1350 muM range with the different enzymes, and the highest affinity found by using these molecules was seen for the pullulanase from Bacillus acidopullulyticus. Both barley-malt limit dextrinase and pullulanase type II from Thermococcus hydrothermalis only recognised the longest linear thiooligosaccharide, while a branched heptasaccharide was the strongest inhibitor of pullulanase from Klebsiella planticola.

  DOI：

  10.1002/1521-3765(20021202)8:23<5447::aid-chem5447>3.0.co;2-h
• 作为产物：
  描述：

  (2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose 在 吡啶 、 camphor-10-sulfonic acid 、 氢氟酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.5h， 生成 (2,3,6-tri-O-acetyl-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Chemoenzymatic Syntheses of Linear and Branched Hemithiomaltodextrins as Potential Inhibitors for Starch-Debranching Enzymes

  摘要：

  Oligosaccharides embodying the S-maltosyl-6-thiomaltosyl structure have been readily synthesised by using convergent chemoenzymatic approaches. The key steps for the preparation of these molecules involved: 1) transglycosylation reactions of maltosyl fluorides onto suitable acceptors catalysed by the bacterial transglycosylase, cyclodextrin glycosyltransferase (CGTase), and 2) the S(N)2-type displacement of a 6-halide from acetylated acceptors by activated 1-thioglycoses. The target molecules, which were obtained in good overall yields, proved to be useful for investigating substrate binding in the active sites of several enzymes that act upon the alpha-1,6-linkage of pullulan and/or amylopectin. The compounds exhibit K-i values in the 2.5-1350 muM range with the different enzymes, and the highest affinity found by using these molecules was seen for the pullulanase from Bacillus acidopullulyticus. Both barley-malt limit dextrinase and pullulanase type II from Thermococcus hydrothermalis only recognised the longest linear thiooligosaccharide, while a branched heptasaccharide was the strongest inhibitor of pullulanase from Klebsiella planticola.

  DOI：

  10.1002/1521-3765(20021202)8:23<5447::aid-chem5447>3.0.co;2-h