1,5-anhydro-D-fructose | 109212-90-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-D-fructose
• 英文别名: 1,5-Anhydro D-Fructose 2-Hydrate；(4S,5S,6R)-6-(hydroxymethyl)oxane-3,3,4,5-tetrol
• CAS: 109212-90-0
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: XFOMARSOADLZQX-WDCZJNDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-D-fructose 、 蔗糖 在 sodium acetate 作用下， 以 重水 为溶剂， 生成 α-D-glucopyranosyl-(1->6)-O-1,5-anhydro-D-fructose 、 α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->6)-O-1,5-anhydro-D-fructose 、 α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->6)-α-D-glucopyranosyl-(1->6)-O-1,5-anhydro-D-fructose
  参考文献：
  名称：

  A novel family of glucosyl 1,5-anhydro-d-fructose derivatives synthesised by transglucosylation with dextransucrase from Leuconostoc mesenteroides NRRL B-512F

  摘要：

  1,5-Anhydro-D-fructose (AF), a metabolite of starch/glycogen degradation, is a good antioxidant. With the prospect of increasing its applications and use as a food ingredient, AF glucosylation catalysed by the dextransucrase from Leuconostoc mesenteroides NRRL B-512F was performed in the presence of sucrose. This led to AF glucosylated derivatives containing alpha-(1-->6) linkages named 1,5-anhydro-D-fructo-glucooligosaccharides (AFGOS). LC-MS analyses showed that AFGOS with a degree of polymerisation (DP) of up to 7 were synthesised. The amount of AFGOS produced and the average DP increased by using a high sucrose/AF molar ratio and high total sugar concentration. AFGOS were proved to present antioxidant properties quite similar to AF. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2004.10.026
• 作为产物：
  描述：

  1,5-无水葡萄糖醇 在 pyranose 2-oxidase 、 catalase 作用下， 以 水 为溶剂， 反应 9.0h， 以98%的产率得到1,5-anhydro-D-fructose
  参考文献：
  名称：

  Rare Keto-Aldoses from Enzymatic Oxidation: Substrates and Oxidation Products of Pyranose 2-Oxidase

  摘要：

  DOI：

  10.1002/(sici)1521-3765(19981204)4:12<2442::aid-chem2442>3.0.co;2-a

文献信息

• Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (−)-bissetone and (−)-palythazine
  作者：Manfred Brehm、Volker H. Göckel、Pan Jarglis、Frieder W. Lichtenthaler

  DOI：10.1016/j.tetasy.2008.01.019

  日期：2008.2

  High-yielding protocols are described to convert D-glucose-via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and beta-elimination of acid-into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio- and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-D-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale. (C) 2008 Elsevier Ltd. All rights reserved.
• 1,5-ANHYDRO-D-FRUCTOSE SUBSTITUTED WITH A HYDROPHOBIC GROUP FOR USE AS ANTI-OXIDANT AND/OR EMULSIFIER
  申请人：DANISCO A/S

  公开号：EP1163248B1

  公开（公告）日：2004-09-22
• Rare Keto-Aldoses from Enzymatic Oxidation: Substrates and Oxidation Products of Pyranose 2-Oxidase
  作者：Stefan Freimund、Alexander Huwig、Friedrich Giffhorn、Sabine Köpper

  DOI：10.1002/(sici)1521-3765(19981204)4:12<2442::aid-chem2442>3.0.co;2-a

  日期：1998.12.4
• A novel family of glucosyl 1,5-anhydro-d-fructose derivatives synthesised by transglucosylation with dextransucrase from Leuconostoc mesenteroides NRRL B-512F
  作者：Gaëtan Richard、Shukun Yu、Pierre Monsan、Magali Remaud-Simeon、Sandrine Morel

  DOI：10.1016/j.carres.2004.10.026

  日期：2005.2

  1,5-Anhydro-D-fructose (AF), a metabolite of starch/glycogen degradation, is a good antioxidant. With the prospect of increasing its applications and use as a food ingredient, AF glucosylation catalysed by the dextransucrase from Leuconostoc mesenteroides NRRL B-512F was performed in the presence of sucrose. This led to AF glucosylated derivatives containing alpha-(1-->6) linkages named 1,5-anhydro-D-fructo-glucooligosaccharides (AFGOS). LC-MS analyses showed that AFGOS with a degree of polymerisation (DP) of up to 7 were synthesised. The amount of AFGOS produced and the average DP increased by using a high sucrose/AF molar ratio and high total sugar concentration. AFGOS were proved to present antioxidant properties quite similar to AF. (C) 2004 Elsevier Ltd. All rights reserved.