Kojic acid-tripeptide amide as a new tyrosinase inhibitor.
Twenty two kojic acid-tripeptide amides were prepared using a solid-phase Fmoc/tBu strategy with Rink Amide SURE(R) resin. To effectively obtain kojic acid-tripeptide amide conjugates, the coupling conditions of kojic acid to the tripeptide on the resin were optimized. The tyrosinase inhibitory activity of kojic acid-tripeptide amides and the effect of the amino acid sequence on the activity were compared with those of kojic acid-tripeptide acids. The stability of kojic acid-tripeptide amides were then compared with those of kojic acid and kojic acid-tripeptides acids. As a consequence, kojic acid-FWY-NH(2) proved to be the best compound, with the highest inhibitory activity, which was maintained over different storage times under various temperatures and pHs.
Noh
Jin-Mi
JM
School of Chemical and Biological Engineering, Seoul National University, Seoul, Republic of Korea.
Kwak
Seon-Yeong
SY
Kim
Do-Hyun
DH
Lee
Yoon-Sik
YS
D004355:Drug Stability; D004791:Enzyme Inhibitors / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015394:Molecular Structure; D014442:Monophenol Monooxygenase / Q000037:antagonists & inhibitors*; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D011753:Pyrones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D013329:Structure-Activity Relationship
D004791:Enzyme Inhibitors; D009842:Oligopeptides; D011753:Pyrones; C011890:kojic acid; D014442:Monophenol Monooxygenase