4-deoxy-4-methoxy-L-erythrulose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-deoxy-4-methoxy-L-erythrulose
• 英文别名: (3S)-1,3-dihydroxy-4-methoxybutan-2-one；1,3-dihydroxy-4-methoxybutan-2-one
• 化学式: C₅H₁₀O₄
• 分子量: 134.132
• InChiKey: CUCFRLBWEWEHAO-YFKPBYRVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-deoxy-4-methoxy-L-erythrulose 、 三氟乙酸酐 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 以99%的产率得到
  参考文献：
  名称：

  A thermostable transketolase evolved for aliphatic aldehyde acceptors

  摘要：

  通过定向进化，一种热稳定性转酮醇酶的进化产物具有显著提高的催化活性、对映选择性和底物范围。

  DOI：

  10.1039/c4cc08436e
• 作为产物：
  描述：

  3-羟基-2-氧代丙酸 、 甲氧基乙醛 在 转酮醇酶 thiamine pyrophosphate 、 magnesium chloride 作用下， 以 水 为溶剂， 生成 4-deoxy-4-methoxy-L-erythrulose
  参考文献：
  名称：

  Enzyme-catalyzed synthesis of carbohydrates: synthetic potential of transketolase

  摘要：

  The synthetic potential of yeast or spinach transketolases was studied, using hydroxypyruvate as a donor substrate and 31 aldehydes as acceptors. All of them react, including aromatic, heteroaromatic and alpha,beta unsaturated aldehydes.

  DOI：

  10.1016/s0040-4039(00)93434-8

文献信息

• Study of the specificity of a spinach transketolase on achiral substrates
  作者：Valérie Dalmas、Colette Demuynck

  DOI：10.1016/s0957-4166(00)80106-8

  日期：1993.11

  The behaviour and the specificity of a spinach transketolase towards achiral aldehydes was studied. We have shown that these aldehydes are accepted by the enzyme and yield the corresponding saccharides with good enantiomeric excess.
• Application of a modified Mosher’s method for the determination of enantiomeric ratio and absolute configuration at C-3 of chiral 1,3-dihydroxy ketones
  作者：James L. Galman、Helen C. Hailes

  DOI：10.1016/j.tetasy.2009.07.023

  日期：2009.8

  The enantiomeric ratio and absolute configuration of products of the transketolase reaction are typically determined by comparison of the specific rotation or derivatisation and HPLC or GC. A Mosher's ester method has been developed via ester formation at the primary alcohol C-1 which can be used to determine the stereoselectivity of the reaction, as well as the absolute configuration of the product at C-3. (c) 2009 Elsevier Ltd. All rights reserved.
• Enzyme-catalyzed synthesis of carbohydrates: synthetic potential of transketolase
  作者：Colette Demuynck、Jean Bolte、Laurence Hecquet、Valérie Dalmas

  DOI：10.1016/s0040-4039(00)93434-8

  日期：1991.9

  The synthetic potential of yeast or spinach transketolases was studied, using hydroxypyruvate as a donor substrate and 31 aldehydes as acceptors. All of them react, including aromatic, heteroaromatic and alpha,beta unsaturated aldehydes.
• A thermostable transketolase evolved for aliphatic aldehyde acceptors
  作者：Dong Yi、Thangavelu Saravanan、Titu Devamani、Franck Charmantray、Laurence Hecquet、Wolf-Dieter Fessner

  DOI：10.1039/c4cc08436e

  日期：——

  Directed evolution of a thermostable transketolase yields catalysts with significant improvement in activity, enantioselectivity and substrate scope.

  通过定向进化，一种热稳定性转酮醇酶的进化产物具有显著提高的催化活性、对映选择性和底物范围。