title: β-galactosidase-catalyzed synthesis of galactosyl chlorphenesin and its characterization.
abstract: We synthesized galactosyl chlorphenesin (CPN-G) using β-gal-containing Escherichia coli (E. coli) cells in which the conversion yield of chlorphenesin (CPN) to CPN-G reached about 64 % during 12 h. CPN-G was identified and characterized using high-performance liquid chromatography, liquid chromatography-mass spectrometry, Fourier transform-infrared spectrometry, and nuclear magnetic resonance analysis ((1)H and (13)C). We verified that a galactose was covalently bound to a CPN alcohol group during CPN-G synthesis throughout these analyses. In particular, by the hydrolysis of CPN-G using β-gal, it was confirmed that a galactose was bound to CPN. The minimal inhibitory concentration (MIC) results showed that the CPN-G MICs were fairly similar to those of CPN. HACAT cell viability was significantly higher in CPN-G-treated cells than in CPN-treated cells at concentrations of 0.0-20.0 mM. Finally, we accomplished the synthesis of less toxic CPN-G, compared with CPN, using β-gal-containing E. coli cells as whole cells without changes in the MICs against microorganisms.
authors.affiliation: Department of Biotechnology, Korea National University of Transportation, Jeungpyung, Chungbuk, 368-701, Republic of Korea.
authors.forename: Sang-Eun
authors.initials: SE
authors.lastname: Lee
authors.forename: Tae-Min
authors.initials: TM
authors.lastname: Jo
authors.forename: Hyang-Yeol
authors.initials: HY
authors.lastname: Lee
authors.forename: Jongsung
authors.initials: J
authors.lastname: Lee
authors.forename: Kyung-Hwan
authors.initials: KH
authors.lastname: Jung
mesh_terms: D055162:Biocatalysis; D002743:Chlorphenesin / Q000737:chemistry / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D004926:Escherichia coli / Q000201:enzymology* / Q000235:genetics / Q000378:metabolism; D029968:Escherichia coli Proteins / Q000235:genetics / Q000378:metabolism*; D005690:Galactose / Q000378:metabolism*; D015394:Molecular Structure; D001616:beta-Galactosidase / Q000737:chemistry / Q000235:genetics / Q000378:metabolism*
chemical_list: D029968:Escherichia coli Proteins; D001616:beta-Galactosidase; D002743:Chlorphenesin; D005690:Galactose