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Abstract
Hyunjong Yua, Kyung-Min Parkb, Pahn-ShickChanga,c,d,*
aDepartment of Agricultural Biotechnology, Seoul National University, Seoul 08826, Republic of Korea
bDepartment of Food Science and Biotechnology, Wonkwang University, Iksan 54538, Republic of Korea
cCenter for Food and Bioconvergence, Seoul National University, Seoul 08826, Republic of Korea
dResearch Institute of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Republic of Korea
*Corresponding author
Abstract
Lipase-catalyzed acylation of a hydrophilic tripeptide-KHA (TP-KHA; amino acid sequence Lys-His-Ala) with a lipophilic lauric acid was performed to produce a multi-functional compound, lauroyl tripeptide-KHA (TPL-KHA), with surface, antibacterial, and antioxidant activities. The significant acylation reaction parameters were optimized as follows: organic solvent of 2-methyl-2-butanol, reaction temperature at 55 °C, substrate molar ratio (lauric acid:TP-KHA) of 4.0, and reaction time for 72 h. Structural analyses by LC-ESI-MS and 1H NMR identified that Nε-lauroyl tripeptide-KHA was chemo-selectively synthesized by the acylation reaction under the optimum conditions. TPL-KHA showed the surface activity at the air–water interface with critical micelle concentration (CMC) of 2.71 mM and γCMC of 30.44 mN/m. TPL-KHA exhibited bacteriostatic and bactericidal effects on Gram-positive and Gram-negative foodborne pathogens (minimum inhibitory concentrations: 2.83–4.00 mM, minimum bactericidal concentrations: 3.17–5.83 mM). Moreover, it was demonstrated that TPL-KHA had the ability to scavenge ABTS+ radicals and inhibit the lipid oxidation.
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