Antibacterial Effect of Fructose Laurate Synthesized by Candida antarctica B Lipase-Mediated Transesterification.
Sugar esters are valuable compounds composed of various sugars and fatty acids that can be used as antibacterial agents and emulsifiers in toothpaste and canned foods. For example, fructose fatty acid esters suppress growth of Streptococcus mutans, a typical pathogenic bacterium causing dental caries. In this study, fructose laurate ester was chosen as a target material and was synthesized by a transesterification reaction using Candida antarctica lipase B. We performed a solvent screening experiment and found that a t-butanol/dimethyl sulfoxide mixture was the best solvent to dissolve fructose and methyl laurate. Fructose laurate was synthesized by transesterification of fructose (100 mM) with methyl laurate (30 mM) in t-butanol containing 20% dimethyl sulfoxide. The conversion yield was about 90%, which was calculated based on the quantity of methyl laurate using high-performance liquid chromatography. Fructose monolaurate (Mr 361) was detected in the reaction mixture by high-resolution mass spectrometry. The inhibitory effect of fructose laurate on growth of oral or food spoilage microorganisms, including S. mutans, Bacillus coagulans, and Geobacillus stearothermophilus, was evaluated.
Department of Biotechnology, The Catholic University of Korea, Bucheon 14662, Republic of Korea.
Ki Ppeum
KP
Lee
Department of Biotechnology, The Catholic University of Korea, Bucheon 14662, Republic of Korea.
Hyung Kwoun
HK
Kim
D000900:Anti-Bacterial Agents / Q000378:metabolism / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002851:Chromatography, High Pressure Liquid; D004951:Esterification; D005632:Fructose / Q000378:metabolism / Q000494:pharmacology; D005656:Fungal Proteins / Q000378:metabolism*; D007848:Laurates / Q000378:metabolism / Q000494:pharmacology; D008049:Lipase / Q000378:metabolism*; D008826:Microbial Sensitivity Tests; D013696:Temperature
D000900:Anti-Bacterial Agents; D005656:Fungal Proteins; D007848:Laurates; D005632:Fructose; D008049:Lipase; C431349:lipase B, Candida antarctica
Lipase; antimicrobial activity; fructose laurate; sugar ester; transesterification