(2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-1,2,4,6-tetra-O-acetyl-D-glucopyranose | 215775-94-3

• 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-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-1,2,4,6-tetra-O-acetyl-D-glucopyranose
• 英文别名: (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1->4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1->3)-1,2,4,6-tetra-O-acetyl-D-glucopyranose；O¹,O²,O⁴,O⁶-Tetraacetyl-O³-[O²,O³,O⁶-triacetyl-O⁴-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranosyl]-ξ-D-glucopyranose；Glc2Ac3Ac4Ac6Ac(b1-4)Glc2Ac3Ac6Ac(b1-3)Glc1Ac2Ac4Ac6Ac；[(2R,3R,4S,5R,6S)-4,5-diacetyloxy-3-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxy-6-[(3R,4S,5R,6R)-2,3,5-triacetyloxy-6-(acetyloxymethyl)oxan-4-yl]oxyoxan-2-yl]methyl acetate
• CAS: 215775-94-3
• 化学式: C₄₀H₅₄O₂₇
• 分子量: 966.853
• InChiKey: HZYWNJCAJGXDBU-ROFQTSFXSA-N

物化性质

• 沸点：
  853.5±65.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 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：
  335
• 氢给体数：
  0
• 氢受体数：
  27

反应信息

• 作为反应物：
  描述：

  (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-1,2,4,6-tetra-O-acetyl-D-glucopyranose 在 甲醇 、 sodium hydroxide 、 氢溴酸 、 sodium methylate 、 苄基三乙基溴化铵 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 3,5-dinitrophenyl β-D-glucopyranosyl-(1-4)-β-D-glucopyranosyl-(1-3)-β-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of aryl 3-O-β-cellobiosyl-β-d-glucopyranosides for reactivity studies of 1,3-1,4-β-glucanases

  摘要：

  A series of substituted aryl beta-glycosides derived from 3-O-beta-cellobiosyl-D-glucopyranose with different phenol-leaving group abilities as measured by the pK(a) of the free phenol group upon enzymatic hydrolysis has been synthesised. Aryl beta-glycosides with a pK(a) of the free phenol leaving group > 5 were prepared by phase-transfer glycosidation of the per-O-acetylated alpha-glycosyl bromide with the corresponding phenol, whereas the 2,4-dinitrophenyl beta-glycoside was obtained by condensation of 1-fluoro-2,4-dinitrobenzene with the partially acetylated trisaccharide followed by acid de-O-acetylation. The aryl beta-glycosides have been used for reactivity studies of the wild-type Bacillus licheniformis 1,3-1,4-beta-D-glucan 4-glucanohydrolase. The Hammett plot log k(cat) versus pK(a) is biphasic with an upward curvature at low pK(a) values suggesting a change in transition-state structure depending on the aglycon. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00175-x
• 作为产物：
  描述：

  乙酸酐 、 alkaline earth salt of/the/ methylsulfuric acid 在 吡啶 、 1,3-1,4-β-glucanase (from Bacillus licheniforms) 、 水 作用下， 生成 (2,3,4,6-tetra-O-acetyl-β-D-glucoyranosyl)-(1-4)-(2,3,6-tri-O-acetyl-β-D-glucopyranosyl)-(1-3)-1,2,4,6-tetra-O-acetyl-D-glucopyranose
  参考文献：
  名称：

  Synthesis of aryl 3-O-β-cellobiosyl-β-d-glucopyranosides for reactivity studies of 1,3-1,4-β-glucanases

  摘要：

  A series of substituted aryl beta-glycosides derived from 3-O-beta-cellobiosyl-D-glucopyranose with different phenol-leaving group abilities as measured by the pK(a) of the free phenol group upon enzymatic hydrolysis has been synthesised. Aryl beta-glycosides with a pK(a) of the free phenol leaving group > 5 were prepared by phase-transfer glycosidation of the per-O-acetylated alpha-glycosyl bromide with the corresponding phenol, whereas the 2,4-dinitrophenyl beta-glycoside was obtained by condensation of 1-fluoro-2,4-dinitrobenzene with the partially acetylated trisaccharide followed by acid de-O-acetylation. The aryl beta-glycosides have been used for reactivity studies of the wild-type Bacillus licheniformis 1,3-1,4-beta-D-glucan 4-glucanohydrolase. The Hammett plot log k(cat) versus pK(a) is biphasic with an upward curvature at low pK(a) values suggesting a change in transition-state structure depending on the aglycon. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(98)00175-x

文献信息

• Synthesis of Complex Oligosaccharides by Using a Mutated (1,3)--D-Glucan Endohydrolase from Barley
  作者：Jon K. Fairweather、Maria Hrmova、Simon J. Rutten、Geoffrey B. Fincher、Hugues Driguez

  DOI：10.1002/chem.200304733

  日期：2003.6.6

  Complex oligosaccharides with newly formed (1,3)-beta-glycosidic linkages were obtained in good to excellent yields when substituted or unsubstituted alpha-laminaribiosyl fluorides, acting as donors, were condensed onto mono- and disaccharide beta-D-hexopyranoside acceptors by using a (1,3)-beta-D-glycosynthase. These linear and branched (1,3)-beta-linked oligosaccharides could prove to be important

  当取代或未取代的α-laminaribiosyl氟化物，作为供体，通过缩合生成单糖和二糖β-D-己基吡喃糖苷受体时，可以良好的产率获得具有新形成的（1,3）-β-糖苷键的复杂寡糖。 （1,3）-β-D-糖基合成酶。这些线性和分支的（1,3）-β-连接的寡糖在医疗，制药和农业应用领域中可能被证明是重要的。此外，观察到（1,3）-β-D-葡聚糖葡糖合酶在其受体亚位点中容纳了（1,3）-，（1,4），-和（1,6）-β-寡糖，但来自高等植物的野生型（1,3）-β-D-葡聚糖内切酶的生理作用却出乎意料。
• Unfermentable Sugars in Barley Mash fermented by the Amylo Process
  作者：HIDEO ONO、MICHIO DAZAI

  DOI：10.1038/1831055b0

  日期：1959.4

  IN an earlier communication1 concerning the production of alcohol from starchy materials by the amylo process, it was demonstrated that sugar consumption with barley fell considerably below that of the other raw materials by failing to exceed 85 per cent even with barley grains from which the bran had been removed. This was attributed to the presence of a considerable amount of unfermentable sugars. We now wish to report on the composition of residual unfermentable sugars in the fermented mash of barley, including the isolation of laminaribiose and of a β-linked glucosyl trisaccharide from this mash.

  在早先关于用阿米洛工艺从淀粉原料中生产酒精的通信1 中，证明了大麦的耗糖量大大低于其他原料的耗糖量，即使是去掉麸皮的大麦粒，耗糖量也不超过 85%。这是因为存在大量的不发酵糖。我们现在要报告的是大麦发酵醪中残留的未发酵糖的成分，包括从这种醪中分离出的层压木糖和一种δ-连接葡糖基三糖。
• SELECTIVE ENZYMOLYSIS OF POLY-β-<scp>D</scp>-GLUCANS, AND THE STRUCTURE OF THE POLYMERS
  作者：F. W. Parrish、A. S. Perlin、E. T. Reese

  DOI：10.1139/v60-284

  日期：1960.11.1

  The soluble poly-β-D-glucan from oats has been subjected to degradation by two different types of enzymes. "Cellulase" converts the polysaccharide to a trisaccharide, 4-O-β-D-lamina-ribiosyl-D-glucose, and two tetrasaccharides, 3′-O-β-D-cellobiosyl-D-cellobiose and 4′-O-β-D-laminaribiosyl-D-cellobiose. Degradation by the second enzyme, "laminarinase", produces a trisaccharide, 3-O-β-D-cellobiosyl-D-glucose, and a tetrasaccharide, 3-O-β-D-cellotriosyl-D-glucose. These products, which account for 75-85% of the polymer in each experiment, have been characterized by chemical methods. The data show that the glucan is composed almost entirely of two types of structural sequences: one is a tetrameric unit in which a single β-(1 → 3) linkage alternates with two β-(1 → 4) linkages, and the other, a pentameric unit in which a single β-(1 → 3) linkage alternates with three consecutive β-(1 → 4) linkages.The soluble poly-β-D-glucan from barley has been shown by enzymolysis with the "cellulase" to be closely related in detailed structure to the oat polymer.Steric aspects of the enzymic degradations are discussed.

  燕麦中可溶性聚β-D-葡聚糖经过两种不同类型的酶降解。 "纤维素酶"将多糖转化为三糖，即4-O-β-D-拉曼核糖基-D-葡萄糖，以及两个四糖，即3'-O-β-D-纤维二糖基-D-纤维二糖和4'-O-β-D-拉曼核糖基-D-纤维二糖。第二种酶"Laminarinase"的降解产物是三糖，即3-O-β-D-纤维三糖基-D-葡萄糖，和四糖，即3-O-β-D-纤维三糖基-D-葡萄糖。这些产物在每个实验中占聚合物的75-85％，并通过化学方法进行了表征。数据表明，聚糖几乎完全由两种结构序列组成：一种是四聚体单元，其中单个β-(1 → 3)键交替出现两个β-(1 → 4)键，另一种是五聚体单元，其中单个β-(1 → 3)键交替出现三个连续的β-(1 → 4)键。通过"纤维素酶"对大麦中可溶性聚β-D-葡聚糖的酶解显示其与燕麦聚合物在详细结构上密切相关。讨论了酶降解的立体方面。
• Orthogonal Active-Site Labels for Mixed-Linkage endo-β-Glucanases
  作者：Namrata Jain、Kazune Tamura、Guillaume Déjean、Filip Van Petegem、Harry Brumer

  DOI：10.1021/acschembio.1c00063

  日期：2021.10.15
• Expeditious synthesis of a new hexasaccharide using transglycosylation reaction catalyzed by Bacillus (1→3),(1→4)-β-d-glucan 4-glucanohydrolase
  作者：Josep-Lluı́s Viladot、Bruce Stone、Hugues Driguez、Antoni Planas

  DOI：10.1016/s0008-6215(98)00212-2

  日期：1998.9

  Enzymatic hydrolysis of barley (1-->3),(1-->4)-beta-D-glucan using a recombinant (1-->3),(1-->4)-beta-glucanase from Bacillus licheniformis gives Glc beta 4Glc beta 3Glc isolated after acetylation in 49% yield. Conventional treatment produced the corresponding beta-fluoride which was carefully de-O-acetylated. A transglycosylation reaction with this substrate, catalyzed by the title enzyme, gave Glc beta 4Glc beta 3Glc beta 4Glc beta 4Glc beta 3Glc in 20% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.