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One‐Pot Enzymatic Synthesis of Cyclic Vicinal Diols from Aliphatic Dialdehydes via Intramolecular C−C Bond Formation and Carbonyl Reduction Using Pyruvate Decarboxylases and Alcohol Dehydrogenases
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2018-09-13 , DOI: 10.1002/adsc.201800455
Yan Zhang 1, 2 , Peiyuan Yao 1, 2 , Yunfeng Cui 2 , Qiaqing Wu 1, 2 , Dunming Zhu 1, 2
Affiliation  

An enzymatic cascade reaction was developed for one‐pot enantioselective conversion of aliphatic dialdehydes to chiral vicinal diols using pyruvate decarboxylases (PDCs) and alcohol dehydrogenases (ADHs). The PDCs showed promiscuity in catalysing the cyclization of aliphatic dialdehydes through intramolecular stereoselective carbon‐carbon bond formation. Consequently, 1,2‐cyclopentanediols in three different stereoisomeric forms and 1,2‐cyclohexanediols in two different stereoisomeric forms could be prepared with high conversion and stereoisomeric ratio from the respective initial substrates, glutaraldehyde and adipaldehyde. These cascade reactions represent a promising approach to the biocatalytic synthesis of important chiral vicinal diols.

中文翻译:

丙酮酸脱羧酶和乙醇脱氢酶通过分子内C-C键形成和羰基还原反应从脂肪族二醛一锅法合成环状邻苯二酚

开发了一种酶联级联反应,可使用丙酮酸脱羧酶(PDC)和醇脱氢酶(ADH)将脂肪族二醛单手对映体转化为手性邻位二醇。PDCs通过分子内立体选择性碳-碳键形成催化脂族二醛的环化反应是混杂的。因此,可以从相应的初始底物戊二醛和己二醛以高转化率和立体异构比制备三种不同立体异构形式的1,2-环戊二醇和两种不同立体异构形式的1,2-环己二醇。这些级联反应代表重要手性邻位二醇的生物催化合成的有前途的方法。
更新日期:2018-09-13
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