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Multienzymatic preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid
Tetrahedron: Asymmetry Pub Date : 4 August 2010 , DOI: 10.1016/j.tetasy.2010.07.007
Patrizia Di Gennaro , Silvana Bernasconi , Fulvia Orsini , Erika Corretto , Guido Sello

The use of two oxidoreductases (an aldoketo reductase from Escherichia coli JM109 and an alcohol dehydrogenase from Lactobacillus brevis) has demonstrated that it is possible to prepare enatiomerically pure diols in a one-pot operation. The reactions were applied to the synthesis of (1R)-1-[3-(hydroxymethyl)phenyl]ethanol and (1S)-1-phenylethane-1,2-diol, using a two-step procedure. The yield is nearly quantitative and the enantiomeric purity is greater than 95%. A third step has been introduced by adding a cell biocatalyst showing dihydrodiol dehydrogenase activity from Pseudomonas fluorescens N3. This allows for the preparation of 3-[(1R)-1-hydroxyethyl]benzoic acid and (2S)-hydroxy(phenyl)ethanoic acid.

中文翻译:

3-[(1R)-1-羟乙基]苯甲酸和(2S)-羟基(苯基)乙酸的多酶制备

两种氧化还原酶(来自大肠杆菌JM109的醛糖还原酶和来自短乳杆菌的醇脱氢酶)的使用已证明可以在一锅操作中制备对映体纯的二醇。使用两步方法将反应物用于(1 R)-1- [3-(羟甲基)苯基]乙醇和(1S)-1-苯基乙烷-1,2-二醇的合成。产率几乎是定量的,对映体纯度大于95%。通过添加显示出来自荧光假单胞菌N3的二氢二醇脱氢酶活性的细胞生物催化剂,引入了第三步骤。这允许制备3-[((1R)-1-羟乙基]苯甲酸和(2S)-羟基(苯基)乙酸。
更新日期:2017-01-31
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