2,3-di-O-acetyl-β-D-glucopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose | 72718-62-8

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3-di-O-acetyl-β-D-glucopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose
• 英文别名: 1,2,3,6,2',3'-hexa-O-acetyl-β-lactose；1,2,3,6,2',3'-hexa-O-acetyl-β-D-lactose；Gal2Ac3Ac(b1-4)b-Glc1Ac2Ac3Ac6Ac；[(2R,3R,4S,5R,6S)-4,5,6-triacetyloxy-3-[(2S,3R,4S,5S,6R)-3,4-diacetyloxy-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS: 72718-62-8
• 化学式: C₂₄H₃₄O₁₇
• 分子量: 594.524
• InChiKey: JWXINSMWFMIRCL-RWNQQKCBSA-N

物化性质

• 沸点：
  661.2±55.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  41
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  226
• 氢给体数：
  2
• 氢受体数：
  17

反应信息

• 作为反应物：
  描述：

  2,3-di-O-acetyl-β-D-glucopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose 在 甲醇 、 水 、 sodium methylate 、 silver carbonate 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 204.0h， 生成 magnesium 5-acetamide-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate-(2→6)-β-D-galactopyranosyl-(1→4)-(α/β)-D-glucopyranose
  参考文献：
  名称：

  6'-SIALYLLACTOSE SALTS AND PROCESS FOR THEIR SYNTHESIS AND FOR THE SYNTHESIS OF OTHER ALPHA-SIALYLOLIGOSACCHARIDES

  摘要：

  本发明涉及一种合成α-唾液酸寡糖的方法，特别是6'-唾液酸乳糖及其盐的合成方法，包括通过Koenigs-Knorr反应耦合的步骤，在条件允许其在工业规模上使用的情况下进行。

  公开号：

  US20120071441A1
• 作为产物：
  描述：

  1,2,3,6,2',3'-hexa-O-acetyl-4',6'-O-p-methoxybenzylidene-β-D-lactose 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 4.5h， 以50%的产率得到2,3-di-O-acetyl-β-D-glucopyranosyl-(1->4)-1,2,3,6-tetra-O-acetyl-β-D-glucopyranose
  参考文献：
  名称：

  [EN] 6"-SIALYLLACTOSE SALTS AND PROCESS FOR THEIR SYNTHESIS AND FOR THE SYNTHESIS OF OTHER A-SIALYLOLIGOSACCHARIDES
  [FR] SELS DE 6'-SIALYLLACTOSE ET PROCÉDÉ POUR LEUR SYNTHÈSE ET POUR LA SYNTHÈSE D'AUTRES ?-SIALYL-OLIGOSACCHARIDES

  摘要：

  本发明涉及一种α-唾液酸寡糖的合成过程，尤其是6'-唾液酸乳糖及其盐的合成过程，其中包括一步Koenigs-Knorr反应的偶联步骤，在工业规模下使用的条件下进行。

  公开号：

  WO2010116317A1

文献信息

• Chemoenzymatic Synthesis of a Bifunctionalized Cellohexaoside as a Specific Substrate for the Sensitive Assay of Cellulase by Fluorescence Quenching
  作者：Viviane Boyer、Sébastien Fort、Torben P. Frandsen、Martin Schülein、Sylvain Cottaz、Hugues Driguez

  DOI：10.1002/1521-3765(20020315)8:6<1389::aid-chem1389>3.0.co;2-#

  日期：2002.3.15

  A new bifunctionalized cellohexaose derivative was synthesized as a specific substrate for continuous assay of cellulases by resonance energy transfer. This cellohexaoside has a naphthalene moiety (EDANS) as a fluorescent energy donor at the reducing end and a 4-(4'-dimethylaminobenzeneazo)-benzene derivative as an acceptor chromophore at the non-reducing end. The key steps for the preparation of the

  合成了一种新的双功能纤维六糖衍生物作为特定底物，用于通过共振能量转移连续测定纤维素酶。该纤维六糖苷在还原端具有萘部分（EDANS）作为荧光能量供体，在非还原端具有4-（4'-二甲基氨基苯偶氮）-苯衍生物作为受体生色团。制备靶分子的关键步骤涉及纤维二糖基和纤维四糖基氟化物供体的糖基化反应到腐殖质纤维素酶Cel7B的E197A突变体催化的纤维二糖基受体上。用各种纤维素酶消化后，能量转移被破坏，并且观察到荧光增加。
• Optimized design and synthesis of chemical dimerizer substrates for detection of glycosynthase activity via chemical complementation
  作者：Haiyan Tao、Pamela Peralta-Yahya、Hening Lin、Virginia W. Cornish

  DOI：10.1016/j.bmc.2006.06.034

  日期：2006.10

  Glycosynthases catalyze the formation of a glycosidic bond between a glycosyl fluoride donor substrate and a glycosyl acceptor substrate with high yield, thus providing a valuable approach for the synthesis of carbohydrates and glycoconjugates. Chemical complementation can be used to link glycosynthase activity to the transcription of a reporter gene in vivo, providing a selection for the directed evolution of glycosynthase enzymes with improved properties. In this approach, glycosynthase activity is detected as covalent coupling between a small molecule disaccharide acceptor substrate and a small molecule disaccharide alpha-fluoro donor substrate. Here we report the optimized design and synthesis of these small molecule substrates. These optimized substrates are shown to give a robust, glycosynthase-dependent transcriptional read-out in the chemical complementation assay. The full synthesis and characterization of these substrates are reported for the first time. These optimized chemical dimerizer substrates should allow the potential of chemical complementation for the directed evolution of glycosynthases with diverse substrate specificities and improved properties to be fully realized. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis of O-α-L-fucopyranosyl-(1→6)-O-β-D-galactopyranosyl-(1→4)-D-glucopyranose (6′-O-α-L-fucopyranosyllactose
  作者：Hans H. Baer、Saeed A. Abbas

  DOI：10.1016/s0008-6215(00)85376-8

  日期：1980.8