(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose | 139952-97-9

• 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-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: Glc2Ac3Ac6Ac(a1-4)b-Glc1Ac2Ac3Ac6Ac；[(2R,3R,4S,5R,6R)-4,5-diacetyloxy-3-hydroxy-6-[(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-2-(acetyloxymethyl)oxan-3-yl]oxyoxan-2-yl]methyl acetate
• CAS: 139952-97-9
• 化学式: C₂₆H₃₆O₁₈
• 分子量: 636.561
• InChiKey: VBCQANBCKDVMTB-PCIRLDFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  44
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  232
• 氢给体数：
  1
• 氢受体数：
  18

反应信息

• 作为反应物：
  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 、 氢氟酸 作用下， 反应 0.5h， 以95%的产率得到(2,3,6-tri-O-acetyl-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
• 作为产物：
  描述：

  1-Acetoxybenzotriazol 、 1,2,3,6-tetra-O-acetyl-4-O-(2,3-di-O-acetyl-α-D-glucopyranosyl)-β-D-glucopyranose 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以73%的产率得到(2,3,6-tri-O-acetyl-α-D-glucopyranosyl)-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  麦芽糖和麦芽三糖的光不稳定衍生物作为猪胰α-淀粉酶中麦芽糖糊精结合位点亲和标记的配体

  摘要：

  3-氮杂丁基通过硫与麦芽糖和麦芽三糖的异头位置相连，从而产生光不稳定的硫代糖苷3-氮杂丁基1-硫代-α-麦芽糖苷（11）和3-氮杂丁基1-硫代-α-麦芽三糖苷（12），到麦芽糖的4'-和6'-位置，得到硫醚4'-S-（3-氮杂丁基）-4'-硫代麦芽糖（8）和6'-S-（3-氮杂丁基）-6'-硫代麦芽糖（15）。这四种化合物都是猪胰腺α-淀粉酶作用的良好竞争性抑制剂。当与蛋白质一起辐照时，化合物12使酶不可逆地失活至大约100％。其他化合物的效果要差得多。酶结合位点的不同区域可能被不同的配体化学修饰。

  DOI：

  10.1016/0008-6215(92)80011-o

文献信息

• Further examples of orthoesterification under kinetically controlled conditions application to the selective acylation of sucrose, maltose and α,α-trehalose
  作者：Mohamed Bouchra、Jacques Gelas

  DOI：10.1016/s0008-6215(97)00208-5

  日期：1997.12

  Orthoesterification of sucrose with 1,1-dimethoxyethene under kinetic control gave 4,6-O-methoxyethylidenesucrose in 77% crude yield. Similar orthoesterification of maltose led essentially after acetylation to 1,2,3,6,2',3'-hexa-O-acetyl-4'-6'-O-methoxyethylidenemaltose. Analogous treatment of alpha,alpha-trehalose gave 2,3,2',3'-tetra-O-acetyl-4,6:4',6'-di-O-methoxyethylidene-alpha,alpha-trehalose in 47% yield. The acid-catalyzed opening of these orthoesters was studied, and these reactions were shown to give disaccharides selectively protected by acetyl groups. (C) 1998 Elsevier Science Ltd.