1'-deoxy-1'-fluorosucrose | 77453-90-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1'-deoxy-1'-fluorosucrose
• 英文别名: Fruf1F(b2-1a)Glc；(2R,3R,4S,5S,6R)-2-[(2R,3S,4S,5R)-2-(fluoromethyl)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 77453-90-8
• 化学式: C₁₂H₂₁FO₁₀
• 分子量: 344.291
• InChiKey: JNCCBCIBJGNIDD-UGDNZRGBSA-N

物化性质

• 沸点：
  654.3±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)：
  -3.2
• 重原子数：
  23
• 可旋转键数：
  5
• 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

• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-1-O-(trifluoromethanesulfonyl)-β-D-fructopyranose 在 Bio-Rad AG 50W-X₈ 、 sucrose synthetase 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 9.0h， 生成 1'-deoxy-1'-fluorosucrose
  参考文献：
  名称：

  Synthesis of 1'-deoxy-1'-fluorosucrose via sucrose synthetase mediated coupling of 1-deoxy-1-fluorofructose with uridine diphosphate glucose

  摘要：

  DOI：

  10.1021/ja00330a051

文献信息

• Radiosynthesis of the fluorinated sucrose analogue, 1′-[¹⁸F]fluoro-1′-deoxysucrose
  作者：Andrew N. Gifford、Caitlin V. Bennett、Joanna S. Fowler

  DOI：10.1002/jlcr.2969

  日期：2012.10

  Fluorinated and deoxysucrose analogues have been proven useful in probing the substrate specificity and roles of sucrose processing enzymes and transporters in plants. To synthesize an 18F-labeled fluorodeoxysucrose analogue suitable for in vivo studies, an acyl-protected, disaccharide-based radiofluorination precursor (sucrose 1′-O-trifluoromethanesulfonyl-2,3,4,6,3′,4′,6′-hepta-O-acetate; 2) was prepared by regioselective mono-deacetylation of sucrose octaacetate using a commercial esterase enzyme followed by conversion of the resultant sucrose heptaacetate to the corresponding triflate. Reaction of this triflate precursor with [18F]fluoride followed by base hydrolysis to remove the acetate groups and HPLC purification gave 1′-[18F]fluoro-1′-deoxysucrose (4) in an overall synthesis time of 80 min and with a median decay corrected yield of 26% (n = 4). This study demonstrates the use of an enzymatic approach to aid the synthesis of a regiospecific radiofluorination precursor starting from the readily available fully acetylated sugar, thus avoiding the need for a complex classical carbohydrate protection strategy to individually protect each hydroxyl group in the molecule. Copyright © 2012 John Wiley & Sons, Ltd.

  氟化和脱氧蔗糖类似物已被证明在探究植物中蔗糖加工酶和转运蛋白的底物特异性及其作用方面非常有用。为了合成一种适合体内研究的18F标记的氟脱氧蔗糖类似物，制备了一种酰基保护的基于二糖的放射氟化前体（蔗糖 1'-O-三氟甲磺酰-2,3,4,6,3′,4′,6′-七乙酰酸酯；2），该前体通过使用商业酯酶对蔗糖八乙酸酯进行区域选择性的单脱乙酰化而获得，随后将得到的蔗糖七乙酸酯转化为相应的三氟酸盐。将该三氟酸盐前体与[18F]氟化物反应，并随后通过碱性水解去除乙酸酯基团，经过高效液相色谱（HPLC）纯化，最终在总合成时间为80分钟的情况下获得了1′-[18F]氟-1′-脱氧蔗糖（4），其中位衰变修正产率为26%（n=4）。本研究展示了一种酶促方法，帮助从 readily available 的完全乙酰化糖出发合成一个区域特异性的放射氟化前体，从而避免了对分子中每个羟基进行复杂的传统碳水化合物保护策略的需要。版权 © 2012 John Wiley & Sons, Ltd.
• Characterization of Recombinant Sucrose Synthase 1 from Potato for the Synthesis of Sucrose Analogues
  作者：Ulrike Römer、Nadja Nettelstroth、Walter Köckenberger、Lothar Elling

  DOI：10.1002/1615-4169(200108)343:6/7<655::aid-adsc655>3.0.co;2-a

  日期：2001.8

  The characteristics and the application of recombinant sucrose synthase 1 (SuSy1) from potato for the synthesis of sucrose analogues are described. With UDP-Glc as donor substrate SuSy1 accepts a variety of ketoses, e.g., 1-deoxy-1-fluoro-D-fructose (6; 100%), L-sorbose (7, 55%), and D-xylulose (8; 42%), as well as aldoses, e.g., D-talose (15; 36%), D-idose (16; 24%), D-lyxose (12; 48%), L-arabinose

  介绍了马铃薯重组蔗糖合酶1（SuSy1）在合成蔗糖类似物方面的特点和应用。使用 UDP-Glc 作为供体底物 SuSy1 接受多种酮糖，例如 1-脱氧-1-氟-D-果糖 (6; 100%)、L-山梨糖 (7, 55%) 和 D-木酮糖 (8 ; 42%)，以及醛糖，例如 D-塔罗糖 (15; 36%)、D-艾杜糖 (16; 24%)、D-来苏糖 (12; 48%)、L-阿拉伯糖 (13; 36%) ) 和 D-核糖 (14; 7%)。动力学分析显示非天然受体 6 (kcat/Km = 3.5 s -1 mM -1)、7 (kcat/Km = 1⋅10 -2 s -1 mM -1)、8 (kcat/Km = 2 ⋅10 -2 s -1 mM -1) 和 12 (kcat/Km = 2⋅10 -2 s -1 mM -1) 与 D-果糖 (5; kcat/Km = 34.1 s) 相比是相对较差的底物-1
• Chemical Synthesis of 1′-Deoxy-1′-fluorosucrose
  作者：Weijiang Ying、Vikram Gaddam、Michael Harmata

  DOI：10.1021/ol401044h

  日期：2013.6.7

  The first chemical synthesis of 1'-deoxy-1'-fluorosucrose has been accomplished in eight steps from sucrose by an unlikely, but ultimately successful, S(N)2 displacement reaction.
• Synthesis of 1'-deoxy-1'-fluorosucrose via sucrose synthetase mediated coupling of 1-deoxy-1-fluorofructose with uridine diphosphate glucose
  作者：Peter J. Card、William D. Hitz

  DOI：10.1021/ja00330a051

  日期：1984.9