Oxazolidinone Synthesis through Halohydrin Dehalogenase-Catalyzed Dynamic Kinetic Resolution

被引：22
|
作者：
Mikleusevic, Ana [1 ]
Hamersak, Zdenko [1 ]
Salopek-Sondi, Branka [1 ]
Tang, Lixia [2 ]
Janssen, Dick B. [3 ]
Elenkov, Maja Majeric [1 ]
机构：
[1] Rudjer Boskovic Inst, Zagreb 10000, Croatia
[2] Univ Elect Sci & Technol China, Chengdu, Peoples R China
[3] Univ Groningen, Groningen Biomol Sci & Biotechnol Inst, Biochem Lab, NL-9747 AG Groningen, Netherlands
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2015年 / 357卷 / 08期
关键词：
cyanates; dynamic kinetic resolution; enzyme catalysis; epoxides; halohydrin dehalogenase; oxazolidinones; ENZYME; RACEMIZATION;
D O I：
10.1002/adsc.201500111
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
An efficient dynamic kinetic resolution protocol using a single enzyme is described. Both the kinetic resolution and substrate racemization are catalyzed by halohydrin dehalogenase from Agrobacterium radiobacter AD1 (HheC). The HheC-catalyzed reaction of epibromohydrin and 2-bromomethyl-2-methyloxirane with sodium cyanate afforded 5-substituted 2-oxazolidinones in high yields (97% and 87%) and high optical purity (89% and > 99% ee) in the presence of catalytic amounts of bromide ion. These compounds are valuable building blocks with diverse synthetic applications.
引用
收藏
页码：1709 / 1714
页数：6
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