Functional Characterization of a Novel Dactylosporangium Esterase and Its Utilization in the Asymmetric Synthesis of (R)-Methyl Mandelate.
One novel esterase DAEst6 was identified from the genome of Dactylosporangium aurantiacum subsp. Hamdenensis NRRL 18085. DAEst6 was further characterized to be an esterase which exhibited high resistance to high pH values. Esterase DAEst6 could resolve racemic methyl mandelate and generate (R)-methyl mandelate, one key drug intermediate, with an enantiomeric excess and a conversion of 99 and 49 %, respectively, after process optimization. The optimal working condition for the preparation of (R)-methyl mandelate through DAEst6 was found to be 10-mM racemic methyl mandelate, no organic co-solvents, pH 7.5, and 40 °C, for 5 h. Our work was the first report about the functional characterization of one novel Dactylosporangium esterase and the utilization of one Dactylosporangium esterase in kinetic resolution. Dactylosporangium esterases represented by DAEst6 possess great potential in the generation of valuable chiral drug intermediates and chemicals.
Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China.|University of Chinese Academy of Sciences, Beijing, 100049, People's Republic of China.|Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China.
Dun
D
Deng
Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China.|Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China.
Yun
Y
Zhang
Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China.|Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China.
Aijun
A
Sun
Key Laboratory of Tropical Marine Bio-resources and Ecology, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China. yunfeng.hu@scsio.ac.cn.|Guangdong Key Laboratory of Marine Materia Medica, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou, 510301, People's Republic of China. yunfeng.hu@scsio.ac.cn.|South China Sea Bio-Resource Exploitation and Utilization Collaborative Innovation Center, Guangzhou, People's Republic of China. yunfeng.hu@scsio.ac.cn.
Yunfeng
Y
Hu
D039903:Actinobacteria / Q000201:enzymology*; D000595:Amino Acid Sequence; D003902:Detergents / Q000494:pharmacology; D004795:Enzyme Stability / Q000187:drug effects; D004950:Esterases / Q000737:chemistry / Q000302:isolation & purification / Q000378:metabolism*; D004952:Esters / Q000378:metabolism; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D007477:Ions; D007700:Kinetics; D008333:Mandelic Acids / Q000737:chemistry* / Q000378:metabolism*; D008670:Metals / Q000494:pharmacology; D010802:Phylogeny; D016415:Sequence Alignment; D020539:Sequence Analysis, Protein; D012997:Solvents / Q000494:pharmacology; D013379:Substrate Specificity / Q000187:drug effects; D013501:Surface-Active Agents / Q000494:pharmacology; D013696:Temperature; D013997:Time Factors
D003902:Detergents; D004952:Esters; D007477:Ions; D008333:Mandelic Acids; D008670:Metals; D012997:Solvents; D013501:Surface-Active Agents; C414090:methyl mandelate; D004950:Esterases
(R)-methyl mandelate; Dactylosporangium; High enantiomeric excess; Kinetic resolution; Novel esterase