β-D-fructofuranosyl α-D-arabino-hexopyranosidulose | 78261-84-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: β-D-fructofuranosyl α-D-arabino-hexopyranosidulose
• 英文别名: 2-keto-sucrose；2-ketosucrose；(2R,4S,5S,6R)-2-[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-one
• CAS: 78261-84-4
• 化学式: C₁₂H₂₀O₁₁
• 分子量: 340.284
• InChiKey: UNLJIUHGWSAFMT-YJAJZVKWSA-N

物化性质

• 沸点：
  720.0±60.0 °C(Predicted)
• 密度：
  1.77±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.5
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  β-D-fructofuranosyl α-D-arabino-hexopyranosidulose 在 硼氘化钠 作用下， 以 水 为溶剂， 生成 <2-(2)H>sucrose
  参考文献：
  名称：

  β-D-Fructofuranosyl α-D-arabino-hexopyranosid-2-ulose (2-ketosucrose)

  摘要：

  DOI：

  10.1016/s0008-6215(00)80403-6
• 作为产物：
  描述：

  蔗糖 在 pyranose-2-oxidase EC 1.1.3.10 air 作用下， 以 水 为溶剂， 反应 24.0h， 以100%的产率得到β-D-fructofuranosyl α-D-arabino-hexopyranosidulose
  参考文献：
  名称：

  Novel carbonyl-group-containing dextran synthesis by pyranose-2-oxidase and dextransucrase

  摘要：

  The carbonyl polysaccharide, keto-dextran, was synthesized by the regioselective oxidation of sucrose and by the subsequent transfer reaction of the oxidized sucrose. The regioselective oxidation of sucrose was performed by bioconversion with pyranose-2-oxidase (EC 1.1.3.10). After 24 h, the conversion percentage of sucrose into keto-sucrose was 100% as determined by a colorimetric method with dinitrophenylhydrazine. Converted keto-sucrose was polymerized to keto-dextran by dextransucrase (EC 2.4.1.5). Polymerization of keto-dextran was confirmed by the increase in molecular weight and amount of keto-dextran produced. The amount of keto-dextran produced decreased to 80% of the amount of dextran produced owing to the substrate recognition of DSase. From a Lineweaver-Burk reciprocal plot, the Michaelis constants for sucrose and keto-sucrose were 4.6 mmol L-1 and 14.0 mmol L-1, respectively. The keto-dextran had a carbonyl group in all glucose units. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.06.027

文献信息

• Bromine oxidation of 1,2-O-isopropylidene-α-d-Glucofuranose and sucrose
  作者：Rolf Andersson、Olle Larm、Elisabeth Scholander、Olof Theander

  DOI：10.1016/0008-6215(80)90006-3

  日期：1980.1

  Abstract Sucrose and 1,2-O- isopropylidene-α- d -glucofuranose ( 1 ) were oxidised with bromine in aqueous solution at pH 7 and room temperature. The resulting keto derivatives were converted into their more-stable O -methyloximes, which were characterised by spectroscopic and chromatographic methods. Oxidation of 1 occurred at C-3 and C-5, with a preference for C-5. In the sucrose derivatives isolated

  摘要在室温，pH 7和水溶液中，用溴将蔗糖和1,2-O-异亚丙基-α-d-葡萄糖呋喃糖（1）氧化。将得到的酮衍生物转化为它们更稳定的O-甲基肟，通过光谱和色谱法对其进行表征。在C-3和C-5处发生1的氧化，优先选择C-5。在氧化后分离的蔗糖衍生物中，在吡喃葡萄糖基部分中具有酮基的那些优先。轴向呋喃呋喃糖基糖苷配基保护了吡喃葡萄糖基中的位置3，并且仅在C-2和C-4处发生氧化。还发现了在果糖呋喃糖基部分中在C-3处被氧化的少量蔗糖。