3-Deoxy-DL-glycero-tetrose | 143106-66-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3-Deoxy-DL-glycero-tetrose
• 英文别名: rac-2,4-dihydroxybutanal；2,4-dihydroxy-butyraldehyde；2,4-Dihydroxy-butyraldehyd；Butandiol-(2.4)-al-(1)；2,4-Dihydroxybutanal
• CAS: 143106-66-5
• 化学式: C₄H₈O₃
• 分子量: 104.106
• InChiKey: NKVLMFFGFYHDNE-UHFFFAOYSA-N

物化性质

• 沸点：
  292.8±30.0 °C(Predicted)
• 密度：
  1.192±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  7
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  57.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-羟基-2-氧代丙酸 、 3-Deoxy-DL-glycero-tetrose 在 sodium hydroxide 、 焦磷酸硫胺素 、 Lithium hydroxypyruvate 、 magnesium chloride 作用下， 以 水 为溶剂， 以7%的产率得到5-deoxy-D-threo-hex-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
• 作为产物：
  描述：

  3-羟基-2-甲氧基四氢呋喃 在 Dowex AG-50W-X₈ (H(+) form) 水 作用下， 反应 36.0h， 生成 3-Deoxy-DL-glycero-tetrose
  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

• Donor Promiscuity of a Thermostable Transketolase by Directed Evolution: Efficient Complementation of 1-Deoxy-<scp>d</scp> -xylulose-5-phosphate Synthase Activity
  作者：Thangavelu Saravanan、Sebastian Junker、Michael Kickstein、Sascha Hein、Marie-Kristin Link、Jan Ranglack、Samantha Witt、Marion Lorillière、Laurence Hecquet、Wolf-Dieter Fessner

  DOI：10.1002/anie.201701169

  日期：2017.5.2

  Enzymes catalyzing asymmetric carboligation reactions typically show very high substrate specificity for their nucleophilic donor substrate components. Structure‐guided engineering of the thermostable transketolase from Geobacillus stearothermophilus by directed in vitro evolution yielded new enzyme variants that are able to utilize pyruvate and higher aliphatic homologues as nucleophilic components

  催化不对称碳连接反应的酶通常对其亲核供体底物组分显示很高的底物特异性。通过定向体外进化对源自嗜热脂肪热地芽孢杆菌的热稳定的转酮醇酶进行结构导向的工程改造，产生了新的酶变体，该变体能够利用丙酮酸和更高的脂肪族同源物作为亲核组分进行酰基转移，而不是天然的多羟基化酮糖磷酸酯或羟基丙酮酸。单个突变体H102T证明对3-甲基-2-氧代丁酸酯作为供体的打击最大，而双突变体H102L / H474S对丙酮酸作为供体则显示出最高的催化效率。后一种变体能够补充大肠杆菌的营养缺陷型dxs基因缺失产生的细胞，该基因编码进入萜类生物合成的第一个重要步骤的活性，从而提供了机会进行生长选择测试以进一步优化酶。
• Deoxygenated and alkylated furanoses: Thorpe—Ingold effects on tautomeric equilibria and rates of anomerization
  作者：Joseph R. Snyder、Anthony S. Serianni

  DOI：10.1016/0008-6215(91)80110-9

  日期：1991.3

  to significantly affect both the thermodynamics and kinetics of furanose anomerization. Increased substitution enhances the proportion of cyclic forms in solution by stimulating furanose kclose. In contrast, furanose kopen was less affected by the degree of substitution; however, kinetic studies of 2-deoxyfuranose anomerization implicate furanose ring conformation as a potential determinant of kopen

  2-脱氧-D-甘油四糖，3-脱氧-DL-甘油四糖，3-脱氧-3,3-二-C-甲基-DL-甘油四糖，3-C-甲基-DL-赤藓糖，已经制备了3-C-甲基-DL-苏糖，2-脱氧-5-O-甲基-D-赤戊糖和3-脱氧-5-O-甲基-D-赤戊糖。 -在异头碳上被取代，并通过1H-（300和620 MHz）和13C-nmr（75 MHz）光谱表征。在水溶液（2H2O）中确定环状（α和β呋喃糖酶）和非环状（醛和水合物）形式的比例，并通过1H和13C饱和度测量开环（kopen）和开环（kclose）速率常数。 -转移NMR光谱在p2H 5.0（乙酸缓冲液）和60度下进行。发现呋喃糖环取代的程度显着影响呋喃糖异构化的热力学和动力学。通过刺激呋喃糖闭合，增加的取代增加了溶液中环状形式的比例。相比之下，呋喃糖kopen受取代度的影响较小。然而，对2-脱氧呋喃糖进行异构化反应的动力学研究表明，呋喃糖环的构象可能是kopen的潜在决定因素。
• 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.