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http://dx.doi.org/10.12925/jkocs.2021.38.3.824

Confirmation of Enzymatic Synthesis of 1, 2-Octanediol Galactoside using Mass Spectrometry and NMR Spectroscopy  

Lee, Hyang-Yeol (Department of Biotechnology, Korea National University of Transportation)
Jin, Hong-Jong (KPT Co., LTD)
An, Seung Hye (Department of Biotechnology, Korea National University of Transportation)
Lee, Hye Won (Department of Biotechnology, Korea National University of Transportation)
Jung, Kyung-Hwan (Department of Biotechnology, Korea National University of Transportation)
Publication Information
Journal of the Korean Applied Science and Technology / v.38, no.3, 2021 , pp. 824-831 More about this Journal
Abstract
1, 2-Octanediol galactoside (OD-gal) has been synthesized from 1, 2-octanediol (OD), as a safer cosmetic preservative, using recombinant Escherichia coli β-galactosidase (β-gal). To confirm the molecular structure of synthesized OD-gal, mass spectrometry and NMR (1H- and 13C-) spectroscopy of OD-gal were carried out. In the reaction mixture, a sodium adduct ion of OD-gal (m/z=331.1732) was identified using mass spectrometry analysis. In addition, 1H NMR spectrum of OD-gal showed multiple peaks corresponding to the galactosyl group, which is evidence of galactosylation on OD. Downfield proton peaks at δH 4.39 ppm and multiple peaks from δH 3.98~3.55 ppm were indicative of galactosylation on OD. Up field proton peaks at δH 1.52~1.26 ppm and 0.89 ppm showed the presence of CH2 and CH3 protons of OD. 13C NMR spectrum revealed the presence of 24 carbons suggestive of α- and β-anomers of OD-gal. Among 14 carbon peaks from each anomer, the 4 peaks at δC 31.4, 29.0, 22.3, and 13.7 ppm were assigned to be overlapped showing only 24 peaks out of a total of 28 peaks. The mass value from mass spectrometry analysis of OD-gal, and 1H and 13C NMR spectral data were in good agreement with the expecting structure of OD-gal. Finally, we identified a galactose molecule from the hydrolysate of OD-gal using β-gal. We are expecting that through future study it will eventually be able to develop a safe cosmetic preservative.
Keywords
1, 2-Octanediol galactoside; ${\beta}$-Galactosidase; NMR spectroscopy; Mass spectrometry; Cosmetic preservative;
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Times Cited By KSCI : 2  (Citation Analysis)
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1 K. -H. Jung, H. -Y. Lee, "Escherichia coli β-galactosidase-catalyzed synthesis of 2-phenoxyethanol galactoside and its characterization", Bioprocess and Biosystems Engineering, Vol.38, No.2, pp. 365-372, (2015).   DOI
2 H. -Y. Lee, K. -H. Jung, "Enzymatic synthesis of 2-phenoxyethanol galactoside by whole cells of β-galactosidase-containing Escherichia coli", Journal of Microbiology and Biotechnology, Vol.24, No.9, pp. 1254-1259, (2014).   DOI
3 Y. O. Kim, K. -H. Jung, "Enzymatic synthesis of 1, 2-hexandiol galactoside by whole cells of β-galactosidase-containing recombinant Escherichia coli", Journal of Life Science, Vol.26, No.5, pp. 608-613, (2016).   DOI
4 Y. O. Kim, H. -Y. Lee, K. -H. Jung, "NMR spectroscopy and mass spectrometry of 1, 2-hexanediol galactoside synthesized using Escherichia coli β-galactosidase", J. Korean Oil Chemists' Society", Vol.33, No.2, pp. 286-292, (2016).   DOI
5 J. -S. Kim, K. -H. Jung, "Cytotoxic effects of 1, 2-hexanediol and 1, 2-hexanediol galactoside on HaCaT cell", Journal of the Society of Cosmetic Scientists of Korea, Vol.44, No.3, pp. 343-347, (2018).   DOI
6 K. -H. Jung, "Enhanced enzyme activities of inclusion bodies of recombinant β-galactosidase via the addition of inducer analog after L-arabinose induction in the araBAD promoter system of Escherichia coli", Journal of Microbiology and Biotechnology, Vol.18, No.3, pp. 434-442, (2008).
7 K. -H. Jung, "Purifications of phenoxyethanol galactoside and chlorphenesin galactoside using solvent extraction followed by gel chromatography", Journal of Oil and Applied Science, Vol.34, No.4, pp. 954-961, (2017).   DOI
8 K. -H. Jung, "Optimal conditions for phenylethanol galactoside synthesis using Escherichia coli β-galactosidase", Journal of the Korean Applied Science and Technology, Vol.38, No.1, pp. 99-106, (2021).   DOI
9 E. Lee, S. An, S. A. Cho, Y. Yun, J. Han, Y. K. Hwang, H. K. Kim, T. R. Lee, "The influence of alkane chain length on the skin irritation potential of 1,2-alkanediols", International Journal of Cosmetic Science, Vol.33, Vol.5, pp. 421-425, (2011).   DOI
10 F. C. Kreeshan, J. D. L. Williams, "Allergic contact dermatitis to caprylyl glycol: A novel para-preservative allergen", Contact Dermatitis, Vol.83, No.5, pp. 418-419, (2020).   DOI
11 S. E. Lee, T. M. Jo, H. -Y. Lee, J. Lee, K. -H. Jung, "β -Galactosidase-catalyzed synthesis of galactosyl chlorphenesin and its characterization", Applied Biochemistry and Biotechnology, Vol.171, No.6, pp. 1299-1312, (2013).   DOI
12 W. Johnson Jr., W. F. Bergfeld, D. V. Belsito, R. A. Hill, C. D. Klaassen, D. Liebler, J. G. Marks Jr., R. C. Shank, T. J. Slaga, P. W. Snyder, F. A. Andersen, "Safety assessment of 1, 2-glycols as used in cosmetics", International Journal of Toxicology, Vol.31(Supplement 2), pp.147S-168S, (2012).   DOI
13 H. -Y. Lee, K. -H. Jung, "NMR Spectroscopy and mass spectrometry of phenylethanol galactoside synthesized using Escherichia coli β-galactosidase", Journal of the Korean Applied Science and Technology, Vol.37, No.5, pp. 1323-1329, (2020).   DOI
14 S. E. Lee, H. -Y. Lee, K. -H. Jung, "Production of chlorphenesin galactoside by whole cells of β-galactosidase-containing Escherichia coli", Journal of Microbiology and Biotechnology, Vol.23, No.6, pp. 826-832, (2013).   DOI
15 E. Q. Coelho, S. L. C. Wu, R. S. Nunes, V. M. S. Reis, "Contact urticaria following the use of a cosmetic containing caprylyl glycol: A case report", Contact Dermatitis, Vol.81, No.4, pp. 308-309, (2019).   DOI
16 Y. O. Kim, K. -H. Jung, "β-Galactosidase-catalyzed synthesis of 1, 2-hexanediol galactoside and its purification using ethyl acetate extraction followed by silica gel chromatography", Journal of Korean Oil Chemists' Society, Vol.33 No.3, pp. 498-506, (2016).