(6-bromo-6-deoxy-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl fluoride | 493006-36-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (6-bromo-6-deoxy-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl fluoride
• CAS: 493006-36-3
• 化学式: C₁₇H₂₈BrFO₁₀
• 分子量: 491.306
• InChiKey: MKHWHTHWMAUEQP-STNJEMRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.47
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  147.3
• 氢给体数：
  5.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  (6-bromo-6-deoxy-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-α-D-glucopyranosyl fluoride 在 盐酸 、 cyclodextrin glycosyltransferase 作用下， 以 phosphate buffer 为溶剂， 反应 14.33h， 生成 (2S,3S,4S,5R,6S)-2-Bromomethyl-6-[(2R,3S,4R,5R,6R)-6-((2R,3S,4R,5R,6S)-4,5-dihydroxy-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-3-yloxy)-4,5-dihydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-tetrahydro-pyran-3,4,5-triol
  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-di-O-acetyl-6-bromo-6-deoxy-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranosyl fluoride 在 camphor-10-sulfonic acid 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.5h， 生成 (6-bromo-6-deoxy-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