Knowledge Management System Of Guangzhou Institute of Energy Conversion, CAS
| An efficient chemoenzymatic method to prepare optically active O-methyl-D-serine | |
| Wang, Zhi-Yuan; Lv, Peng-Mei; Yuan, Zhen-Hong; Luo, Wen; Liu, Shu-Na | |
| 2014-09-30 | |
| Source Publication | TETRAHEDRON
 |
| Volume | 70Issue:39Pages:6991-6994 |
| Abstract | Lacosamide is an important anti-epilepsy drug and O-methyl-D-serine is a relevant intermediate in the synthesis of lacosamide. Optically active O-methyl-D-serine was prepared by using a chemoenzymatic method from inexpensive acrylamide. Our method is a four-step reaction sequence: bromination of acrylamide; etherification of dibromopropionamide; ammonolysis of alpha-bromo-beta-methoxy-propionamide; enzymatic racemization and selective hydrolysis. The double-enzyme catalyst system, which consists of alpha-amino-epsilon-caprolactam racemase (Locus, E01594) and D-stereospecific amino-acid amidase (Locus, AB026907), was successfully applied to produce enantiopure O-methyl-D-serine (ee >99.8%) in high yield (>98.5%). Optically active O-methyl-D-serine was obtained with a total yield of 81.3%. (C) 2014 Published by Elsevier Ltd. |
| Subtype | Article |
| Keyword | O-methyl-d-serine Chemoenzymatic Method Alpha-amino-epsilon-caprolactam Racemase D-stereospecific Amino-acid Amidase Lacosamide |
| WOS Headings | Science & Technology ; Physical Sciences |
| DOI | 10.1016/j.tet.2014.07.073 |
| WOS Subject Extended | Chemistry |
| WOS Keyword | EPSILON-CAPROLACTAM RACEMASE ; DYNAMIC KINETIC RESOLUTION ; AMINO-DELTA-VALEROLACTAM ; ACHROMOBACTER-OBAE ; AMINOPEPTIDASE ; PURIFICATION ; MECHANISM |
| Indexed By | SCI ; CCR |
| Language | 英语 |
| WOS Subject | Chemistry, Organic |
| WOS ID | WOS:000341550600011 |
| Citation statistics | |
| Document Type | 期刊论文 |
| Identifier | http://ir.giec.ac.cn/handle/344007/10655 |
| Collection | 中国科学院广州能源研究所 |
| Affiliation | Chinese Acad Sci, Guangzhou Inst Energy Convers, Key Lab Renewable Energy & Gas Hydrate, Guangzhou 510640, Guangdong, Peoples R China |
| Recommended Citation GB/T 7714 | Wang, Zhi-Yuan,Lv, Peng-Mei,Yuan, Zhen-Hong,et al. An efficient chemoenzymatic method to prepare optically active O-methyl-D-serine[J]. TETRAHEDRON,2014,70(39):6991-6994. |
| APA | Wang, Zhi-Yuan,Lv, Peng-Mei,Yuan, Zhen-Hong,Luo, Wen,&Liu, Shu-Na.(2014).An efficient chemoenzymatic method to prepare optically active O-methyl-D-serine.TETRAHEDRON,70(39),6991-6994. |
| MLA | Wang, Zhi-Yuan,et al."An efficient chemoenzymatic method to prepare optically active O-methyl-D-serine".TETRAHEDRON 70.39(2014):6991-6994. |
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