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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
发表期刊TETRAHEDRON
卷号70期号:39页码:6991-6994
摘要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.
文章类型Article
关键词O-methyl-d-serine Chemoenzymatic Method Alpha-amino-epsilon-caprolactam Racemase D-stereospecific Amino-acid Amidase Lacosamide
WOS标题词Science & Technology ; Physical Sciences
DOI10.1016/j.tet.2014.07.073
研究领域[WOS]Chemistry
关键词[WOS]EPSILON-CAPROLACTAM RACEMASE ; DYNAMIC KINETIC RESOLUTION ; AMINO-DELTA-VALEROLACTAM ; ACHROMOBACTER-OBAE ; AMINOPEPTIDASE ; PURIFICATION ; MECHANISM
收录类别SCI ; CCR
语种英语
WOS类目Chemistry, Organic
WOS记录号WOS:000341550600011
引用统计
文献类型期刊论文
条目标识符http://ir.giec.ac.cn/handle/344007/10655
专题中国科学院广州能源研究所
作者单位Chinese Acad Sci, Guangzhou Inst Energy Convers, Key Lab Renewable Energy & Gas Hydrate, Guangzhou 510640, Guangdong, Peoples R China
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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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