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β-Galactosidase-Catalyzed Synthesis of Galactosyl Chlorphenesin and Its Characterization

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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 (1H and 13C). 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.

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Acknowledgement

The research was supported by a grant from the Academic Research Program of Korea National University of Transportation in 2013.

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Authors and Affiliations

  1. Department of Biotechnology, Korea National University of Transportation, Jeungpyung, Chungbuk, 368-701, Republic of Korea

    Sang-Eun Lee, Tae-Min Jo, Hyang-Yeol Lee & Kyung-Hwan Jung

  2. Department of Dermatological Health Management, Eulji University, Seongnam, Gyeonggi, 461-713, Republic of Korea

    Jongsung Lee

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  1. Sang-Eun Lee
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Correspondence to Kyung-Hwan Jung.

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Sang-Eun Lee, Tae-Min Jo, and Hyang-Yeol Lee contributed equally to this work and should be considered as equal first authors.

Korea National University of Transportation is formerly Chungju National University.

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Lee, SE., Jo, TM., Lee, HY. et al. β-Galactosidase-Catalyzed Synthesis of Galactosyl Chlorphenesin and Its Characterization. Appl Biochem Biotechnol 171, 1299–1312 (2013). https://doi.org/10.1007/s12010-013-0213-3

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