4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl fluoride | 7584-85-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl fluoride
• 英文别名: α-maltosyl fluoride；αG2F；α-Maltosylfluorid；alpha-Maltosyl fluoride；(2R,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-fluoro-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 7584-85-2；7792-96-3；30048-41-0；71328-30-8；103531-01-7；149342-82-5；66701-54-0
• 化学式: C₁₂H₂₁FO₁₀
• 分子量: 344.291
• InChiKey: MPJMJSVSVMGORJ-ASMJPISFSA-N

物化性质

• 沸点：
  639.0±55.0 °C(Predicted)
• 密度：
  1.71±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl fluoride 、 α-环糊精 在 pullulanase enzyme 作用下， 反应 1.0h， 生成 6-O-Alpha-麦芽糖基-Alpha-环糊精
  参考文献：
  名称：

  Formation of 6-O-α-maltosylcyclomalto-oligosaccharides from α-maltosyl fluoride and cyclomalto-oligosaccharides by pullulanase

  摘要：

  DOI：

  10.1016/s0008-6215(00)90223-4
• 作为产物：
  描述：

  1,2,3,6,2',3',4',6'-octa-O-acetylmaltose 在 氢氟酸 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 4-O-(α-D-glucopyranosyl)-α-D-glucopyranosyl fluoride
  参考文献：
  名称：

  Formation of 6-O-α-maltosylcyclomalto-oligosaccharides from α-maltosyl fluoride and cyclomalto-oligosaccharides by pullulanase

  摘要：

  DOI：

  10.1016/s0008-6215(00)90223-4

文献信息

• Aqueous Glycosylation of Unprotected Sucrose Employing Glycosyl Fluorides in the Presence of Calcium Ion and Trimethylamine
  作者：Guillaume Pelletier、Aaron Zwicker、C. Liana Allen、Alanna Schepartz、Scott J. Miller

  DOI：10.1021/jacs.5b13384

  日期：2016.3.9

  synthetic glycosylation reaction between sucrosyl acceptors and glycosyl fluoride donors to yield the derived trisaccharides. This reaction proceeds at room temperature in an aqueous solvent mixture. Calcium salts and a tertiary amine base promote the reaction with high site-selectivity for either the 3'-position or 1'-position of the fructofuranoside unit. Because nonenzymatic aqueous oligosaccharide syntheses

  我们报告了蔗糖基受体和糖基氟供体之间的合成糖基化反应，产生衍生的三糖。该反应在室温下在水性溶剂混合物中进行。钙盐和叔胺碱促进反应，对呋喃果糖苷单元的 3'-位或 1'-位具有高位点选择性。由于非酶水性寡糖合成尚不成熟，因此进行了机理研究，以确定选择性的起源，我们假设这与蔗糖中羟基阵列的结构有关。各种单脱氧蔗糖类似物的溶液构象揭示了羟基在同时介导这种水性糖基键形成反应和位点选择性方面的协同性质。
• Streamlined Iterative Assembly of Thio‐Oligosaccharides by Aqueous <i>S</i> ‐Glycosylation of Diverse Deoxythio Sugars
  作者：Peng Wen、Peijing Jia、Qiuhua Fan、Bethany J. McCarty、Weiping Tang

  DOI：10.1002/cssc.202102483

  日期：2022.2.8

  Step by step: A streamlined practical iterative synthesis of S-oligosaccharides is developed in aqueous solution without the need of protecting any of the hydroxy groups. Various deoxythio sugar building blocks can be prepared efficiently. The Ca(OH)2-promoted aqueous S-glycosylation can be realized with high chemo- and stereoselectivity.

  一步一步：在水溶液中开发了S-低聚糖的简化实用迭代合成，无需保护任何羟基。可以有效地制备各种脱氧硫代糖结构单元。 Ca(OH) 2 -促进的水性S-糖基化可以以高化学选择性和立体选择性实现。
• Synthesis of fluorinated maltose derivatives for monitoring protein interaction by ¹⁹F NMR
  作者：Michaela Braitsch、Hanspeter Kählig、Georg Kontaxis、Michael Fischer、Toshinari Kawada、Robert Konrat、Walther Schmid

  DOI：10.3762/bjoc.8.51

  日期：——

  A novel reporter system, which is applicable to the ¹⁹F NMR investigation of protein interactions, is presented. This approach uses 2-F-labeled maltose as a spy ligand to indirectly probe protein–ligand or protein–protein interactions of proteins fused or tagged to the maltose-binding protein (MBP). The key feature is the simultaneous NMR observation of both ¹⁹F NMR signals of gluco/manno-type-2-F-maltose-isomers; one isomer (α-gluco-type) binds to MBP and senses the protein interaction, and the nonbinding isomers (β-gluco- and/or α/β-manno-type) are utilized as internal references. Moreover, this reporter system was used for relative affinity studies of fluorinated and nonfluorinated carbohydrates to the maltose-binding protein, which were found to be in perfect agreement with published X-ray data. The results of the NMR competition experiments together with the established correlation between ¹⁹F chemical shift data and molecular interaction patterns, suggest valuable applications for studies of protein–ligand interaction interfaces.

  介绍了一种新的报告系统，适用于蛋白质相互作用的¹⁹F NMR研究。该方法使用2-F-标记的麦芽糖作为间谍配体，间接探测与融合或标记到麦芽糖结合蛋白（MBP）的蛋白质的蛋白质-配体或蛋白质-蛋白质相互作用。关键特征是同时观察α-葡萄糖型-2-F-麦芽糖异构体的¹⁹F NMR信号；一种异构体（α-葡萄糖型）结合到MBP并感知蛋白质相互作用，而非结合的异构体（β-葡萄糖型和/或α/β-甘露糖型）被用作内部参考。此外，该报告系统用于研究氟化和非氟化碳水化合物与麦芽糖结合蛋白的相对亲和力，发现与已发表的X射线数据完全一致。¹⁹F化学位移数据与分子相互作用模式之间的建立的相关性，以及NMR竞争实验的结果，提示了该系统在研究蛋白质-配体相互作用界面方面的有价值应用。
• Cottaz, Sylvain; Apparu, Christine; Driguez, Hugues, Journal of the Chemical Society. Perkin transactions I, 1991, # 9, p. 2235 - 2241
  作者：Cottaz, Sylvain、Apparu, Christine、Driguez, Hugues

  DOI：——

  日期：——
• Enzymatic synthesis of 3-O-α-maltosyl-l-ascorbate using an engineered cyclodextrin glucanotransferase
  作者：Hee-Jeong Ahn、Chao Li、Hye-Bin Cho、Sunghoon Park、Pahn-Shick Chang、Young-Wan Kim

  DOI：10.1016/j.foodchem.2014.07.110

  日期：2015.2

  A mutant derived from a cyclodextrin glucantransferase with an alanine residue as its acid/base catalyst residue (CGT-E284A) catalyzed regioselective glycosylation at 3-OH of L-ascorbic acid using a-maltosyl fluoride (alpha G2F) and L-ascorbic acid as the donor and acceptor, respectively, yielding 3-O-alpha-maltosyl-L-ascorbate (AA3 alpha G2). The optimum conditions were determined by high-performance liquid chromatography analysis with 20 mM alpha G2F and 40 mM L-ascorbic acid as the substrates at pH 7.5 and 25 degrees C with 1 mg/ml of the enzyme for 24 h. Calcium ions bound in CGT-E284A played an important role in the transglycosylation. CGT-E284A exhibited typical saturation kinetic behaviour for aG2F at a fixed acceptor concentration (40 mM), and substrate inhibition by L-ascorbic acid was observed at high L-ascorbic acid concentrations (>60 mM). AA3 alpha G2 was isolated from a preparative scale reaction with a yield of 29%, and it showed extremely high stability under oxidative conditions. (C) 2014 Elsevier Ltd. All rights reserved.