fructopyranose | 6347-01-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: fructopyranose
• 英文别名: D-fructose；fructose；D-fructopyranose；(3S,4R,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol
• CAS: 6347-01-9
• 化学式: C₆H₁₂O₆
• 分子量: 180.158
• InChiKey: LKDRXBCSQODPBY-VRPWFDPXSA-N

物化性质

• 熔点：
  91.5-93.5 °C
• 沸点：
  401.1±45.0 °C(Predicted)
• 密度：
  1.758±0.06 g/cm3(Predicted)
• 颜色/状态：
  CLEAR COLORLESS LIQUID IN WATER
• 气味：
  ODORLESS
• 味道：
  SWEET
• 碰撞截面：
  141.4 Ų [M+Na]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

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

ADMET

代谢

在缺乏葡萄糖的情况下，果糖通过己糖激酶在细胞质中被磷酸化成果糖-6-磷酸，并且由于对果糖的高米氏常数（KM值）和对葡萄糖的低米氏常数，后者在这种酶的作用下在周围组织中优先被磷酸化。

IN ABSENCE OF GLUCOSE, FRUCTOSE IS PHOSPHORYLATED PERIPHERALLY BY HEXOKINASE TO FRUCTOSE-6-PHOSPHATE, &, ON ACCOUNT OF HIGH KM VALUE FOR FRUCTOSE & LOW KM VALUE FOR GLUCOSE, LATTER IS PREFERENTIALLY PHOSPHORYLATED BY THIS ENZYME IN PERIPHERAL TISSUES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

口服果糖通常在多种动物的肠粘膜上转化为葡萄糖，如豚鼠、仓鼠和狗。新生小猪和一个月以下的幼牛无法利用它。那些葡萄糖-6-磷酸脱氢酶和相关酶缺乏的物种可能难以将其代谢。

ORAL FRUCTOSE IS OFTEN CONVERTED TO GLUCOSE IN INTESTINAL MUCOSA OF A NUMBER OF SPECIES, SUCH AS GUINEA PIG, HAMSTER, & DOG. NEWBORN PIGS & YOUNG CALVES UP TO 1 MO OF AGE CANNOT UTILIZE IT. SPECIES...WITH LOW GLUCOSE-6-PHOSPHATE DEHYDROGENASE & RELATED ENZYME DEFICIENCIES MAY HAVE DIFFICULTY IN METABOLIZING IT.

来源:Hazardous Substances Data Bank (HSDB)

代谢

果糖比葡萄糖更快地被代谢，并且更快地转化为糖原，而这个反应发生不需要胰岛素的存在。当注射相同剂量的果糖时，与给予相同速率的葡萄糖相比，血糖水平更低，溢出也更少。

FRUCTOSE IS MORE RAPIDLY METABOLIZED & MORE QUICKLY CONVERTED TO GLYCOGEN THAN IS DEXTROSE, & PRESENCE OF INSULIN IS NOT NECESSARY FOR THIS REACTION TO TAKE PLACE. WHEN...INJECTED LOWER LEVELS OF BLOOD SUGAR & LESS SPILLAGE RESULT THAN WHEN SIMILAR AMT OF DEXTROSE ARE GIVEN @ SAME RATE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 吸入症状

咳嗽。

Cough.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 眼睛症状

红肿。疼痛。

Redness. Pain.

来源:ILO-WHO International Chemical Safety Cards (ICSCs)

毒理性

• 相互作用

在对照研究中，针对急性酒精中毒患者，大剂量静脉输液......导致血液乙醇水平下降速度的小幅但统计学上显著的增加。......通常解释这种果糖效果的是......糖本身或其代谢物之一增强了酒精脱氢酶的作用。

IN CONTROLLED STUDY OF PATIENTS WITH ACUTE ALCOHOLIC INTOXICATION, IV INFUSION OF LARGE DOSE...CAUSED SMALL BUT STATISTICALLY SIGNIFICANT INCR IN RATE OF FALL OF BLOOD ETHANOL LEVELS. ... USUAL EXPLANATION FOR THIS EFFECT OF FRUCTOSE... IS ENHANCEMENT OF ACTION OF ALC DEHYDROGENASE BY SUGAR ITSELF OR BY ONE OF ITS METABOLITES.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 相互作用

香烟烟雾致突变性的降低通过与添加果糖的烟雾冷凝物的相互作用。

REDUCTION IN MUTAGENICITY OF CIGARETTE SMOKE BY INTERACTION OF SMOKE CONDENSATES WITH ADDED FRUCTOSE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

输注果糖与尿酸产生增加和痛风有关。在患有遗传性果糖不耐受（醛缩酶缺乏）的患者中，果糖可能导致严重反应（低血糖、恶心、呕吐、颤抖、昏迷、抽搐）。

INFUSION OF FRUCTOSE HAS BEEN ASSOCIATED WITH INCREASED URIC ACID PRODUCTION & HYPERURICEMIA. IN PATIENTS WITH HEREDITARY FRUCTOSE INTOLERANCE (ALDOLASE DEFICIENCY), FRUCTOSE CAN CAUSE SEVERE REACTIONS (HYPOGLYCEMIA, NAUSEA, VOMITING, TREMORS, COMA, CONVULSIONS).

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

果糖的浓度可以是葡萄糖的两倍，以相同的速率输注，具有更好的保留效果，并且对流体平衡的干扰更小。

TWICE THE CONCN OF FRUCTOSE CAN BE INFUSED AT THE SAME RATE AS DEXTROSE WITH BETTER RETENTION AND LESS DISTURBANCE OF FLUID BALANCE.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

果糖的优点是它能够迅速从细胞外空间移除，因此，尿液排出量最小化。

...ADVANTAGES OF FRUCTOSE IS ITS RAPID REMOVAL FROM EXTRACELLULAR SPACE, & THEREFORE, URINARY EXCRETION IS MINIMIZED.

来源:Hazardous Substances Data Bank (HSDB)

反应信息

• 作为反应物：
  描述：

  fructopyranose 在 culture of Gluconobactor cerinus (ATCC catalogue number IFO 3267) 作用下， 生成 5-酮果糖
  参考文献：
  名称：

  Antibody-catalysed glycosyl transfer reactions from in vitro immunization

  摘要：

  使用五元环亚胺环醇在体外进行免疫，获得了能够催化对硝基苯基吡喃葡萄糖苷和对硝基苯基吡喃半乳糖苷水解的抗体，其速率增益（kcat/kuncat）超过10,000倍。

  DOI：

  10.1039/a704885h
• 作为产物：
  描述：

  苯基-BETA-葡萄糖吡喃糖苷 在 palladium on activated charcoal pyranose 2-oxidase 、 氢气 、 catalase 作用下， 以 水 为溶剂， 反应 72.0h， 生成 fructopyranose
  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
• 作为试剂：
  描述：

  alpha-酮戊二酸 在 fructopyranose 、 cliona varians 、 对甲苯磺酸 作用下， 以 水 为溶剂， 反应 96.0h， 生成 (–)-(R)-diisopropyl 2-hydroxyglutarate 、 (S)-di-i-propyl 2-hydroxyglutarate
  参考文献：
  名称：

  Biotechnological Properties of Sponges from Northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds

  摘要：

  To research the potential ability of whole marine sponges to act as biocatalysts, this paper describes for the first time the employment of whole Cliona varians sponge in the stereoselective reduction of prochiral alpha-keto esters and isatin to the corresponding chiral alcohols. The addition of D-fructose, D-glucose or sucrose remarkably increased the conversion ratios and stereoselectivities by this marine sponge. Furthermore, in the presence of D-glucose and D-maltose. the reduction of isatin by C. varians afforded the corresponding 3-hydroxyindolin-2-one with high conversions (85-90%) and good enantioselectivities (60-74%). These results showed that the marine sponge presents great potential to be used as biocatalyst for stereoselective reduction of carbonyl compounds.

  DOI：

  10.21577/0103-5053.20180165

文献信息

• Determination of the absolute configuration of monosaccharides by a colour change in a chiral cholesteric liquid crystal system
  作者：Tony D. James、Takaaki Harada、Seiji Shinkai

  DOI：10.1039/c39930000857

  日期：——

  Cholesterylboronic acid complexes of monosaccharides alter the colour of a composite chiral cholesteric liquid crystal membrane, the direction of the colour change is indicative of the absolute configuration of the monosaccharide.

  单糖的胆甾醇硼酸复合物改变复合手性胆甾型液晶膜的颜色，颜色变化的方向指示单糖的绝对构型。
• Quantitation of Monosaccharide Isotopic Enrichment in Physiologic Fluids by Electron Ionization or Negative Chemical Ionization GC/MS Using Di-<i>O</i>-isopropylidene Derivatives
  作者：David L. Hachey、W. Reed Parsons、Siripoom McKay、Morey W. Haymond

  DOI：10.1021/ac990724x

  日期：1999.10.1

  The aldonitrile pentaacetate and other derivatives lack ions in the electron ionization (EI) spectra possessing an intact hexose structure and thus must be analyzed by chemical ionization GC/MS in order to study multiple isotopomers. We report methods for quantitation of hexose di-O-isopropylidene acetate (IPAc) or pentafluorobenzoyl (PFBz) esters. These were prepared in a two-step procedure using inexpensive reagents that do not adversely impact the isotopomer structure of the sugar. The acetate derivative possesses an abundant [M − CH3] ion in the EI spectrum which is suitable for quantitative analysis of isotopomers. The negative chemical ionization (NCI) spectrum of the corresponding pentafluorobenzoyl derivative has a dominant molecular anion. Moreover, the PFBz derivative is about 100-fold more sensitive than the acetate, which offers some advantages for analysis of minor hexoses found in plasma. Isotopic calibration curves of [U-13C]glucose are linear over the 0.1−60% tracer/tracee range tested. The useful range for isotopic tracer studies is 25−2500 pmol for EI analysis of the acetate derivative and 0.1−55 pmol for NCI analysis of PFBz derivative (sample amount injected). For most studies where sample size is not limited, EI-GC/MS analysis of the IPAc derivative is preferred. NCI-GC/MS analysis is reserved when sample size is limiting or when studies involve hexoses other than glucose that are normally present at low concentration.

  aldonitrile pentaacetate和其他具有完整己糖结构的衍生物在电子离子化（EI）光谱中缺乏离子，因此必须通过化学离子化GC/MS分析才能研究多种同位素异构体。我们报告了己糖二-O-异丙叉乙酸酯（IPAc）或五氟苯甲酰（PFBz）酯的定量方法。这些是通过使用廉价试剂的两步程序制备的，这些试剂不会对糖的同位素结构产生不利影响。乙酸酯衍生物在EI光谱中具有丰富的[M - CH3]离子，适合用于同位素异构体的定量分析。相应的五氟苯甲酰衍生物的负化学离子化（NCI）光谱具有主导的分子阴离子。此外，PFBz衍生物的灵敏度大约是乙酸酯的100倍，这为分析在血浆中发现的次要己糖提供了一些优势。[U-13C]葡萄糖的同位素校准曲线在测试的0.1-60%示踪剂/本体范围内是线性的。同位素示踪剂研究的有用范围是25-2500 pmol用于乙酸酯衍生物的EI分析，0.1-55 pmol用于PFBz衍生物的NCI分析（注射的样品量）。对于大多数样本大小不受限制的研究，优先选择IPAc衍生物的EI-GC/MS分析。当样本大小受限或研究涉及通常以低浓度存在的非葡萄糖己糖时，保留NCI-GC/MS分析。
• Porous Tin-Organic Frameworks as Selective Epimerization Catalysts in Aqueous Solutions
  作者：Irina Delidovich、Andreas Hoffmann、Andrea Willms、Marcus Rose

  DOI：10.1021/acscatal.7b00806

  日期：2017.6.2

  Epimerization of sugars is a carbon-efficient route not only to produce rare carbohydrates but also to extend the product scope for chemical production in future biorefineries. Industrially available catalysts for epimerization are limited mainly to soluble Mo(VI) species as well as substrate-specific epimerases. Here we report highly active and selective tin-organic frameworks (Sn-OF) as solid catalysts

  糖的差向异构化是一种碳效率高的途径，它不仅可以生产稀有的碳水化合物，而且可以扩展未来生物精炼厂化学生产的产品范围。工业上可用于差向异构化的催化剂主要限于可溶性Mo（VI）物种以及底物特异性差向异构酶。在这里，我们报告高活性和选择性的锡有机骨架（Sn-OF）作为固态催化剂，用于在C-2位置醛糖的差向异构化，例如葡萄糖转化为甘露糖。该反应通过碳骨架重排进行，即通过破坏C-2 / C-3碳键并形成C-1 / C-3键来进行。部分水解的PH 3发现Sn-OH位点是催化活性中心。我们的结果表明，Sn-OFs对差向异构体的高催化活性取决于（1）锡的路易斯酸度；（2）游离的Sn-OH基团；（3）水溶液中使用的有机连接基的高疏水性。
• Substrate-dependent chemoselective aldose–aldose and aldose–ketose isomerizations of carbohydrates promoted by a combination of calcium ion and monoamines
  作者：Tomoaki Tanase、Tomoyuki Takei、Masanobu Hidai、Shigenobu Yano

  DOI：10.1016/s0008-6215(01)00156-2

  日期：2001.7

  with the CaCl(2) system in CD(3)OD revealed that the C-2 epimerization proceeds via stereospecific rearrangement of the carbon skeleton, or 1,2-carbon shift, and ketose formation proceeds partially through an intramolecular hydrogen migration or 1,2-hydride shift and, in part, via an enediol intermediate. These simultaneous aldose-aldose and aldose-ketose isomerizations showed interesting substrate-dependent

  通过将各种金属离子与二胺，单胺和氨基醇结合使用，对C-2上醛糖的差向异构化进行了广泛的研究。醛基在碱金属或稀土金属离子（Ca（2 +），Sr（2 +），Pr（3+）或Ce（3+））和单胺的结合下在C-2上发生差向异构三乙胺。特别是，Ca（2 +）-三乙胺系统证明有效地促进了醛糖的酮糖-酮糖异构化以及C-2差向异构。使用D-（1-（13）C）葡萄糖和D-（1-（13）C）半乳糖与CaCl（2）系统在CD（3）OD中的13C NMR研究表明，C-2差向异构化是通过立体特异性进行的碳骨架的重排或1，2-碳移位和酮糖的形成部分通过分子内氢迁移或1，2-氢化物移位进行，部分通过烯二醇中间体进行。这些同时的醛糖-醛糖和醛糖-酮糖异构化显示出有趣的底物依赖性化学选择性。具有2,3-赤型构型的甘露糖型醛糖（D-甘露糖，D-lyxose和D-核糖）对C-2差向异构体和醛糖-酮糖异构化均显示出相当大的抗性，而葡萄糖型糖具有2
• [EN] N-SUBSTITUTED MANNOSAMINE DERIVATIVES, PROCESS FOR THEIR PREPARATION AND THEIR USE<br/>[FR] DÉRIVÉS N-SUBSTITUÉS DE MANNOSAMINE, PROCÉDÉ POUR LEUR PRÉPARATION ET LEUR UTILISATION
  申请人：GLYCOM AS

  公开号：WO2012140576A1

  公开（公告）日：2012-10-18

  A compound of the formula (I) wherein R1 is a group removable by hydrogenolysis,and wherein R2 is OH or R2 is -NHR3 wherein R3 is a group removable by hydrogenolysis. The compound can be made from fructose by a Heyns-rearrangement. The compound can be used then to make - free D-mannosamine or its salts, - D-mannosamine building blocks and mannosamine containing oligo- or polysaccharides, - N-acetyl-D-mannosamine and its hydrates and solvates, - neuraminic acid derivatives and, - viral neuraminidase inhibitors.

  公式(I)的化合物，其中R1是可通过氢解去除的基团，且其中R2是OH或R2是-NHR3，其中R3是可通过氢解去除的基团。该化合物可以通过Heyns重排从果糖制备。然后，该化合物可用于制备无游离α-D-甘露糖胺或其盐，α-D-甘露糖胺构建块和含甘露糖胺的寡糖或多糖，N-乙酰-D-甘露糖胺及其水合物和溶剂化物，神经氨酸衍生物以及病毒神经氨酸酶抑制剂。