Functional Characterization of a Robust Marine Microbial Esterase and Its Utilization in the Stereo-Selective Preparation of Ethyl (S)-3-Hydroxybutyrate.
One novel microbial esterase PHE21 was cloned from the genome of Pseudomonas oryzihabitans HUP022 identified from the deep sea of the Western Pacific. PHE21 was heterologously expressed and functionally characterized to be a robust esterase which behaved high resistance to various metal ions, organic solvents, surfactants, and NaCl. Despite the fact that the two enantiomers of ethyl 3-hydroxybutyrate were hard to be enzymatically resolved before, we successfully resolved racemic ethyl 3-hydroxybutyrate through direct hydrolysis reactions and generated chiral ethyl (S)-3-hydroxybutyrate using esterase PHE21. After process optimization, the enantiomeric excess, the conversion rate, and the yield of desired product ethyl (S)-3-hydroxybutyrate could reach 99, 65, and 87 %, respectively. PHE21 is a novel marine microbial esterase with great potential in asymmetric synthesis as well as in other industries.
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.
Yilong
Y
Wang
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. 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
D004795:Enzyme Stability / Q000187:drug effects; D004950:Esterases / Q000302:isolation & purification / Q000378:metabolism*; D006863:Hydrogen-Ion Concentration; D006868:Hydrolysis; D006885:Hydroxybutyrates / Q000737:chemistry / Q000378:metabolism*; D007477:Ions; D007700:Kinetics; D008670:Metals / Q000494:pharmacology; D011549:Pseudomonas / Q000187:drug effects / Q000201:enzymology*; D012623:Seawater / Q000382:microbiology*; D020539:Sequence Analysis, Protein; D012965:Sodium Chloride / Q000494:pharmacology; D012997:Solvents / Q000494:pharmacology; D013237:Stereoisomerism; D013379:Substrate Specificity / Q000187:drug effects; D013501:Surface-Active Agents / Q000494:pharmacology; D013696:Temperature; D013997:Time Factors
D006885:Hydroxybutyrates; D007477:Ions; D008670:Metals; D012997:Solvents; D013501:Surface-Active Agents; D012965:Sodium Chloride; C435833:ethyl 3-hydroxybutyrate; D004950:Esterases
Deep-sea microorganism; Ethyl (S)-3-hydroxybutyrate; High stereo-selectivity; Kinetic resolution; Robust esterase