(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-S-acetyl-1-thio-α-D-glucopyranose | 493006-52-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-S-acetyl-1-thio-α-D-glucopyranose
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-diacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-acetylsulfanyloxan-3-yl]oxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 493006-52-3
• 化学式: C₄₀H₅₄O₂₆S
• 分子量: 982.919
• InChiKey: NFYXKSNMMKBIFE-GOJLZCMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  67
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  352
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  methyl (2,3,6-tri-O-acetyl-6-iodo-6-deoxy-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside 、 (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-S-acetyl-1-thio-α-D-glucopyranose 在 1,4-dithio-erythritol 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以76%的产率得到methyl (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-S-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->6)-(2,3,4-tri-O-acetyl-6-thio-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosy...
  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：

  triphenylmethyl (2,3,6-tri-O-acetyl-4-O-tetrahydropyranyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-thio-α-D-glucopyranoside 在 吡啶 、 三乙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.75h， 生成 (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-S-acetyl-1-thio-α-D-glucopyranose
  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