Enzymatic Synthesis of 1, 2-Hexanediol Galactoside by Whole Cells of β-Galactosidase-containing Recombinant Escherichia coli

β-galactosidse 함유하는 재조합 대장균 세포를 이용한 1,2-hexanediol galactoside의 합성

Kim, Yi-Ok;Jung, Kyung-Hwan

  • Received : 2016.01.21
  • Accepted : 2016.03.28
  • Published : 2016.05.30


Recently, it has been reported that some preservatives used in cosmetics lead to skin problems. Among the many cosmetic ingredients, 1, 2-hexanediol (HD) is used as both a preservative and humectant. In order to develop safer ingredients, we studied the synthesis of 1, 2-hexanediol galactoside (HD-G) by a transgalactosylation reaction using β-galactosidase (β-gal)-containing recombinant Escherichia coli cells. The transgalactosylation reaction was carried out under high-lactose conditions for 24 hr. After 12 hr had elapsed, a new spot was identified by thin-layer chromatography (TLC) analysis, and we presumptively designated this new spot as HD-G. Then, we carried out the purification of the presumptive HD-G spot from the reaction mixture by using silica gel chromatography, and its mass was measured by electrospray ionization-mass spectrometry. The purified new spot on the chromatograph was identified a sodium adduct ion ([M+Na]+, m/z = 303.1423) of HD-G. In addition, when purified HD-G was hydrolyzed using commercially available E. coli β-gal, it was observed that a galactose molecule was released from HD-G. That is, it was demonstrated that HD-G is a galactoside derivative of HD. Finally, we confirmed that HD-G was enzymatically synthesized by E. coli β -gal as a new molecular entity. In the future, we plan to determine the minimum inhibitory concentrations of HD-G against different bacterial species. The cytotoxicity of HD-G against human skin cells will also be examined. It is expected hopefully that the galactosylation of HD would improve the functionality of HD-G.


1, 2-Hexanediol;β-Galactosidase;cosmetic preservative;Escherichia coli;transgalactosylation


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