5,6-dideoxy-D-threo-hex-5-en-2-ulose | 143106-69-8

• 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-dideoxy-D-threo-hex-5-en-2-ulose
• 英文别名: (3S,4R)-1,3,4-trihydroxyhex-5-en-2-one
• CAS: 143106-69-8
• 化学式: C₆H₁₀O₄
• 分子量: 146.143
• InChiKey: ZBDMIKWXYIEVBU-XINAWCOVSA-N

物化性质

• 沸点：
  366.2±37.0 °C(Predicted)
• 密度：
  1.292±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 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：

  5,6-dideoxy-D-threo-hex-5-en-2-ulose 在 phosphate buffer 、 sodium formate 、 臭氧 、 NADH 、 sodium sulfite 作用下， 以 水 为溶剂， 反应 88.0h， 生成 L-木糖
  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
• 作为产物：
  描述：

  3-羟基-2-氧代丙酸 、 (+/-)-2-hydroxy-3-butenal 在 sodium hydroxide 、 焦磷酸硫胺素 、 Lithium hydroxypyruvate 、 magnesium chloride 作用下， 以 水 为溶剂， 反应 96.0h， 以30%的产率得到5,6-dideoxy-D-threo-hex-5-en-2-ulose
  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

• Transketolase from Escherichia coli: A practical procedure for using the biocatalyst for asymmetric carbon-carbon bond synthesis
  作者：K.Gall Morris、Mark E.B. Smith、Nicholas J. Turner、Malcolm D. Lilly、Robin K. Mitra、John M. Woodley

  DOI：10.1016/0957-4166(96)00266-2

  日期：1996.8

  A practical procedure is reported for the use of the enzyme transketolase, from Escherichia coli, for asymmetric carbon-carbon bond synthesis. The reactions with the biocatalyst are conveniently carried out, on a gram scale, in unbuffered aqueous media by employing a pH autotitrator. An improved large scale synthesis of hydroxypyruvate is also reported. Copyright (C) 1996 Elsevier Science Ltd
• 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.