Biocatalytic resolution of glycidyl phenyl ether using a novel epoxide hydrolase from a marine bacterium, Maritimibacter alkaliphilus KCCM 42376 [corrected].
As a continuous effort of developing highly enantioselective epoxide hydrolase from marine microorganisms, it was found that Maritimibacter alkaliphilus KCCM 42376 [corrected] was highly enantioselective toward racemic glycidyl phenyl ether (GPE). An open reading frame (ORF) encoding a putative epoxide hydrolase (EHase) was cloned from the genome of Maritimibacter alkaliphilus KCCM 42376 [corrected], followed by expression and purification in Escherichia coli. The purified EHase (REH) hydrolyzed (S)-GPE preferentially over (R)-GPE. Enantiopure (R)-GPE from kinetic resolution of 29.2 mM racemic GPE using the purified REH could be obtained with enantiopurity of more than 99.9% enantiomeric excess (ee) and 38.4% yield (theoretical, 50%) within 20 min (enantiomeric ratio (E-value): 38.4). The enantioselective activity of REH toward GPE was also confirmed by the analysis of the vicinal diol, 3-phenoxy-1,2-propanediol. To our knowledge, this study demonstrates the highest enantioselective resolution of racemic GPE using a purified biocatalyst among the known native EHases.
Woo
Jung-Hee
JH
Marine Biotechnology Research Centre, Korea Ocean Research and Development Institute, Ansan, P. O. Box 29, 425-600, Korea.
Kang
Ji-Hyun
JH
Hwang
Young-Ok
YO
Cho
Jang-Cheon
JC
Kim
Sang-Jin
SJ
Kang
Sung Gyun
SG
D020561:Alphaproteobacteria / Q000201:enzymology*; D000595:Amino Acid Sequence; D055162:Biocatalysis; D004851:Epoxide Hydrolases / Q000096:biosynthesis / Q000235:genetics / Q000378:metabolism*; D004926:Escherichia coli / Q000235:genetics / Q000378:metabolism; D016680:Genome, Bacterial; D005990:Glycerol / Q000031:analogs & derivatives / Q000032:analysis; D006868:Hydrolysis; D008969:Molecular Sequence Data; D010647:Phenyl Ethers / Q000737:chemistry / Q000378:metabolism*
D010647:Phenyl Ethers; C525361:3-phenoxy-1,2-propanediol; C016050:phenylglycidyl ether; D004851:Epoxide Hydrolases; D005990:Glycerol