5,6,7-trideoxy-D-threo-2-heptulose | 143106-67-6

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 5,6,7-trideoxy-D-threo-2-heptulose
• 英文别名: 5,6,7-trideoxy-D-threo-heptulose；5-Deoxy-5-ethyl-D-xylulose；(3S,4R)-1,3,4-trihydroxyheptan-2-one
• CAS: 143106-67-6
• 化学式: C₇H₁₄O₄
• 分子量: 162.186
• InChiKey: KXJJDTSNGSAHOL-VDTYLAMSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 5,6,7-trideoxy-D-threo-2-heptulose 在 吡啶 作用下， 生成 1,3,4-tri-O-acetyl-5-deoxy-5-ethyl-D-xylulose
  参考文献：
  名称：

  Facile Enzymatic Aldol Reactions with Dihydroxyacetone in the Presence of Arsenate

  摘要：

  Aldol reactions of in situ formed dihydroxyacetone arsenate with different aldehydes were catalyzed by bacterial D-fructose-1,6-bisphosphate aldolase (FruA). Aldolases from bacteria were found to be much more stable and active than FruA from rabbit muscle. Arsenate acts as a phosphate mimic and can, in principle, be used in catalytic amounts. The use of inorganic arsenate and dihydroxyacetone afforded high yields with hydrophobic aldehydes. Cosolvents increased the solubility of hydrophobic aldehydes and afforded higher reaction rates and enzyme stability. Insight is given, for the first time, in the influence of arsenate on the stereoselectivity of the aldol reaction.

  DOI：

  10.1021/jo001766k
• 作为产物：
  描述：

  1,1-dimethoxy-pentan-2-ol 在 Dowex AG-50W-X₈ (H(+) form) sodium hydroxide 、 水 、 焦磷酸硫胺素 、 Lithium hydroxypyruvate 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 36.0h， 生成 5,6,7-trideoxy-D-threo-2-heptulose
  参考文献：
  名称：

  Substrate specificity and carbohydrate synthesis using transketolase

  摘要：

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.

  DOI：

  10.1021/jo00048a023

文献信息

• One-pot four-enzyme synthesis of ketoses with fructose 1,6-bisphosphate aldolases from Staphylococcus carnosus and rabbit muscle
  作者：Zijie Li、Li Cai、Mohui Wei、Peng George Wang

  DOI：10.1016/j.carres.2012.05.007

  日期：2012.8

  By the action of D-fructose 1,6-bisphosphate aldolases (FruA) from rabbit muscle and Staphylococcus carnosus, various ketoses were synthesized from glyceraldehydes or other aliphatic aldehydes as acceptors in a one-pot four-enzyme system.

  通过来自兔肌肉和葡萄球菌的D-果糖1,6-二磷酸醛缩酶（FruA）的作用，在一站式四酶系统中由甘油醛或其他脂族醛作为受体合成了各种酮糖。
• Carbohydrates from glycerol: an enzymatic four-step, one-pot synthesis
  作者：Rob Schoevaart、Fred van Rantwijk、Roger A. Sheldon

  DOI：10.1039/a907874f

  日期：——

  A novel one-pot procedure, involving a cascade of four enzymatic steps, for the synthesis of carbohydrates from glycerol and an aldehyde is reported.

  报告中介绍了一种新颖的一锅式程序，该程序涉及四个酶促步骤，以甘油和醛为原料合成碳水化合物。
• A Four-Step Enzymatic Cascade for the One-Pot Synthesis of Non-natural Carbohydrates from Glycerol
  作者：Rob Schoevaart、Fred van Rantwijk、Roger A. Sheldon

  DOI：10.1021/jo000492y

  日期：2000.10.1

  A total of four enzymatic steps were combined, in a: one-pot reaction, to synthesize carbohydrates starting from glycerol. First, phosphorylation of glycerol by reaction with pyrophosphate in the presence of phytase at pH 4.0 in 95% glycerol afforded racemic glycerol-3-phosphate in 100% yield. The L-enantiomer of the latter underwent selective aerobic oxidation to dihydroxyacetone phosphate (DHAP) at pH 7.5 in the presence of glycerolphosphate oxidase (GPO) and catalase. Subsequently, fructose-1,6-bisphosphate aldolase catalyzed the aldol reaction of DHAP with butanal. Finally, dephosphorylation of the aldol adduct was mediated by phytase at pH 4 affording 5-deoxy-5-ethyl-D-xylulose in, 57% yield from L-glycerol-3-phosphate. The phytase on/off-snitch by pH was the key to controlling phosphorylation and dephosphorylation.
• Substrate specificity and carbohydrate synthesis using transketolase
  作者：Yoshihiro Kobori、David C. Myles、George M. Whitesides

  DOI：10.1021/jo00048a023

  日期：1992.10

  This paper describes the use of the enzyme transketolase as a catalyst in organic synthesis. The properties of transketolase from both yeast and spinach were investigated. The yeast enzyme was found to be more convenient for routine use. Examination of the substrate specificity of yeast transketolase demonstrated that the enzyme accepts a wide variety of 2-hydroxy aldehydes as substrates. A practical protocol for transketolase-catalyzed condensation of hydroxypyruvic acid with these aldehydes has been developed and used for the synthesis of four carbohydrates: L-idose, L-gulose, 2-deoxy-L-xylohexose, and L-xylose.
• Facile Enzymatic Aldol Reactions with Dihydroxyacetone in the Presence of Arsenate
  作者：Rob Schoevaart、Fred Van Rantwijk、Roger A. Sheldon

  DOI：10.1021/jo001766k

  日期：2001.6.1

  Aldol reactions of in situ formed dihydroxyacetone arsenate with different aldehydes were catalyzed by bacterial D-fructose-1,6-bisphosphate aldolase (FruA). Aldolases from bacteria were found to be much more stable and active than FruA from rabbit muscle. Arsenate acts as a phosphate mimic and can, in principle, be used in catalytic amounts. The use of inorganic arsenate and dihydroxyacetone afforded high yields with hydrophobic aldehydes. Cosolvents increased the solubility of hydrophobic aldehydes and afforded higher reaction rates and enzyme stability. Insight is given, for the first time, in the influence of arsenate on the stereoselectivity of the aldol reaction.