2,2',3,3',4',6,6'-hepta-O-acetyl-1-S-acetyl-1-thio-α-maltose | 119803-71-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2',3,3',4',6,6'-hepta-O-acetyl-1-S-acetyl-1-thio-α-maltose
• 英文别名: 2,3,6-tri-O-acetyl-1-S-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-1-thio-α-D-glucopyranose；(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetyl-1-S-acetyl-1-thio-α-D-glucopyranose；[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-2-(acetyloxymethyl)-6-acetylsulfanyloxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 119803-71-3
• 化学式: C₂₈H₃₈O₁₈S
• 分子量: 694.665
• InChiKey: FRXVJYSARLMCLR-QACPWNKNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.11
• 重原子数：
  47.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  228.86
• 氢给体数：
  0.0
• 氢受体数：
  19.0

反应信息

• 作为反应物：
  描述：

  2,2',3,3',4',6,6'-hepta-O-acetyl-1-S-acetyl-1-thio-α-maltose 在 sodium methylate 、 二乙胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 13.0h， 生成 (α-D-glucopyranosyl)-(1->4)-S-(α-D-glucopyranosyl)-(1->6)-(6-thio-α-D-glucopyranosyl)-(1->4)-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
• 作为产物：
  描述：

  triphenylmethyl (2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1->4)-2,3,6-tri-O-acetylthio-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 2,2',3,3',4',6,6'-hepta-O-acetyl-1-S-acetyl-1-thio-α-maltose
  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

文献信息

• Inclusion and solubilization properties of 6-S-glycosyl-6-thio derivatives of β-cyclodextrin
  作者：Valérié Lainé、Annie Coste-Sarguet、Andrée Gadelle、Jacques Defaye、Bruno Perly、Florence Djedaïni-Pilard

  DOI：10.1039/p29950001479

  日期：——

  The synthesis and physico-chemical properties of branched beta-cyclodextrins substituted by one or seven thioglycoside units at the primary hydroxy side are described. The solubilities in water of these compounds are strongly increased compared with the parent beta-cyclodextrin although large differences are found between alpha- and beta-anomers, the former exhibiting the larger solubility. The inclusion capacity of these derivatives has been investigated using NMR spectroscopy as the major analytical technique for various host-guest pairs. The apparent discrepancies between the intrinsic solubilities of these host molecules and their ability to solubilize hydrophobic hosts can be explained from geometrical considerations derived from detailed NMR studies. The respective roles of the:side of inclusion, of steric effects and of stabilizing interactions are evidenced and allow an a priori selection of the optimal host derivative for a given guest molecule.
• Blanc-Muesser, Michele; Driguez, Hugues, Journal of the Chemical Society. Perkin transactions I, 1988, p. 3345 - 3352
  作者：Blanc-Muesser, Michele、Driguez, Hugues

  DOI：——

  日期：——
• BLANC-MUESSER, MICHELE;DRIGUEZ, HUGUES, J. CHEM. SOC. PERKIN TRANS. PT 1,(1988) N2, C. 3345-3351
  作者：BLANC-MUESSER, MICHELE、DRIGUEZ, HUGUES

  DOI：——

  日期：——