(3R,4R)-3,4,5-三羟基-2-氧代戊醛 | 3445-24-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: (3R,4R)-3,4,5-三羟基-2-氧代戊醛
• 英文名称: D-erythro-pentos-2-ulose
• 英文别名: pentos-2-ulose；pentosone；D-erythro-[2]pentosulose；D-ribosone；D-erythro-3,4,5-Trihydroxy-2-oxo-valeraldehyd；D-Arabinoson；d-Arabinosone；(3R,4R)-3,4,5-trihydroxy-2-oxopentanal
• CAS: 3445-24-7
• 化学式: C₅H₈O₅
• 分子量: 148.116
• InChiKey: VDSAQEDKJUSZPS-UHNVWZDZSA-N

物化性质

• 沸点：
  405.9±45.0 °C(Predicted)
• 密度：
  1.499±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• 海关编码：
  2914400090

反应信息

• 作为反应物：
  描述：

  (3R,4R)-3,4,5-三羟基-2-氧代戊醛 在 potassium cyanide 、 氮气 、 水 作用下， 生成 D-异抗坏血酸
  参考文献：
  名称：

  奥森-布劳绍尔-方法论综合与综合

  摘要：

  DOI：

  10.1002/hlca.19340170157
• 作为产物：
  描述：

  阿拉伯糖 在 copper diacetate 作用下， 以 甲醇 、 水 为溶剂， 反应 0.25h， 以29%的产率得到(3R,4R)-3,4,5-三羟基-2-氧代戊醛
  参考文献：
  名称：

  13C-Substituted pentos-2-uloses: synthesis and analysis by 1H- and 13C-n.m.r. spectroscopy

  摘要：

  D-erythro-Pentos-2-ulose and D-threo-pentos-2-ulose and their 1-13C- and 2-13C-substituted derivatives have been prepared by oxidizing the corresponding natural and 13C-substituted D-aldopentoses (D-arabinose, D-xylose) with cupric acetate, and purifying the products by chromatography on a cation-exchange resin in the calcium or barium form. The equilibrium compositions of the pentos-2-uloses in 2H2O were determined by 13C-n.m.r. spectroscopy (75 MHz) at 25 degrees and 80 degrees. Among the eighteen possible monomeric acyclic, cyclic, and bicyclic forms, the anomeric pairs of the unhydrated aldopyranoses, aldopyranose endocyclic hydrates, aldofuranose endocyclic hydrates, and ketofuranose exocyclic hydrates were identified on the basis of 13C chemical shifts and 13C-1H and 13C-13C spin-coupling constants. 1H-N.m.r. (300, 500, and 620 MHz) and 13C-n.m.r. (75 MHz) spectroscopic data in one and two dimensions (DQF-COSY, homonuclear 2D-J) were used to evaluate the conformational properties of the cyclic structures. The unhydrated pyranoses are highly conformationally homogeneous; the erythro and threo isomers prefer 1C4 and 4C1 conformations, respectively. D-threo-Pentos-2-ulopyranose hydrate prefers the 4C1 conformation whereas the erythro isomers exists in both the 4C1 and 1C4 conformations. The furanoid forms favor structures having quasi-axial anomeric hydroxyl groups and quasi-equatorial exocyclic hydroxymethyl or dihydroxymethyl groups.

  DOI：

  10.1016/0008-6215(90)84048-y

文献信息

• Synthesis of d-erythro-2-pentulose and d-threo-2-pentulose and analysis of the 13C- and 1H-n.m.r. spectra of the 1-13C- and 2-13C-substituted sugars
  作者：Tapani Vuorinen、Anthony S. Serianni

  DOI：10.1016/0008-6215(91)80142-a

  日期：1991.1

  immobilized D-xylose (D-glucose) isomerase (E.C.5.3.1.5). The equilibrium compositions of 1 and 2 (furanose anomers and acyclic keto forms) in 2H2O were determined from 13C-n.m.r. spectra (75 MHz) of the 2-13C-labeled derivatives. The conformational properties of the cyclic and acyclic forms in 2H2O were assessed with the use of 1H-1H, 13C-1H, and 13C-13C spin-coupling constants obtained from 1H-n.m.r

  通过氢化相应的同位素正构和13C取代的D-来制备D-赤藓-2-戊糖（1）和D-苏-2-戊糖（2）以及它们的1-13C和2-13C取代的衍生物五氧化二-2-戊糖与钯碳催化剂。所述苏式异构体及其标记的衍生物可替代地由具有固定的D-木糖（D-葡萄糖）异构酶（EC5.3.1.5）的同位素正态和13C-取代的D-木糖制备。由2-13C标记的衍生物的13C-nmr光谱（75 MHz）确定2H2O中1和2（呋喃糖异构体和无环酮形式）的平衡组成。使用从1H-nmr（620 MHz）和13C-nmr（75 MHz）获得的1H-1H，13C-1H和13C-13C自旋耦合常数来评估2H2O中环状和非环状形式的构象性质光谱。与结构上相关的醛呋喃呋喃糖酶相比，2-戊呋喃糖酶更优选其中异头羟基基团准轴向取向的构象。非环状酮形式1和2的强双极化羰基似乎稳定了O-1和O-3被羰基氧取代的链构象。
• Characterization and detection of lysine–arginine cross-links derived from dehydroascorbic acid
  作者：Oliver Reihl、Markus O. Lederer、Wolfgang Schwack

  DOI：10.1016/j.carres.2003.12.004

  日期：2004.2

  Covalently cross-linked proteins are among the major modifications caused by the advanced Maillard reaction. So far, the chemical nature of these aggregates is largely unknown. L-dehydroascorbic acid (DHA, 5), the oxidation product of L-ascorbic acid (vitamin C), is known as a potent glycation agent. Identification is reported for the lysine-arginine cross-links N6-[2-[(4-amino-4-carboxybutyl)amin

  共价交联的蛋白质是由晚期美拉德反应引起的主要修饰。到目前为止，这些聚集体的化学性质基本上是未知的。L-脱氢抗坏血酸（DHA，5）是L-抗坏血酸（维生素C）的氧化产物，被认为是有效的糖基化剂。报告了赖氨酸-精氨酸交联的鉴定N6- [2-[（4-氨基-4-羧基丁基）氨基] -5-（2-羟乙基）-3,5-二氢-4H-咪唑-4-亚烷基] -L-赖氨酸（9），N6- [2-[（[4-氨基-4-羧基丁基）氨基] -5-（1,2-二羟乙基）-3,5-二氢-4H-咪唑-4-亚烷基] -L-赖氨酸（11）和N6- [2-[（（4-氨基-4-羧基丁基）氨基] -5-[（1S，2S）-1,2,3-三羟丙基] -3,5-二氢4H-咪唑-4-亚烷基] -L-赖氨酸（13）。可以从脱氢抗坏血酸（5），降解产物1,3,4-三羟基丁烷-2-一（7，L-赤藓糖），3,4-二羟基-2-氧杂双胍（10，L-苏糖松）和L-苏-戊
• VUORINEN, TAPANI;SERIANNI, ANTHONY S., CARBOHYDR. RES., 209,(1991) C. 13-31
  作者：VUORINEN, TAPANI、SERIANNI, ANTHONY S.

  DOI：——

  日期：——
• Synthese der Ascorbinsäure und verwandter Verbindungen nach der Oson-Blausäure-Methode
  作者：T. Reichstein、A. Grüssner、R. Oppenauer

  DOI：10.1002/hlca.19340170157

  日期：——
• 13C-Substituted pentos-2-uloses: synthesis and analysis by 1H- and 13C-n.m.r. spectroscopy
  作者：Tapani Vuorinen、Anthony S. Serianni

  DOI：10.1016/0008-6215(90)84048-y

  日期：1990.10

  D-erythro-Pentos-2-ulose and D-threo-pentos-2-ulose and their 1-13C- and 2-13C-substituted derivatives have been prepared by oxidizing the corresponding natural and 13C-substituted D-aldopentoses (D-arabinose, D-xylose) with cupric acetate, and purifying the products by chromatography on a cation-exchange resin in the calcium or barium form. The equilibrium compositions of the pentos-2-uloses in 2H2O were determined by 13C-n.m.r. spectroscopy (75 MHz) at 25 degrees and 80 degrees. Among the eighteen possible monomeric acyclic, cyclic, and bicyclic forms, the anomeric pairs of the unhydrated aldopyranoses, aldopyranose endocyclic hydrates, aldofuranose endocyclic hydrates, and ketofuranose exocyclic hydrates were identified on the basis of 13C chemical shifts and 13C-1H and 13C-13C spin-coupling constants. 1H-N.m.r. (300, 500, and 620 MHz) and 13C-n.m.r. (75 MHz) spectroscopic data in one and two dimensions (DQF-COSY, homonuclear 2D-J) were used to evaluate the conformational properties of the cyclic structures. The unhydrated pyranoses are highly conformationally homogeneous; the erythro and threo isomers prefer 1C4 and 4C1 conformations, respectively. D-threo-Pentos-2-ulopyranose hydrate prefers the 4C1 conformation whereas the erythro isomers exists in both the 4C1 and 1C4 conformations. The furanoid forms favor structures having quasi-axial anomeric hydroxyl groups and quasi-equatorial exocyclic hydroxymethyl or dihydroxymethyl groups.