Kojic acid–tripeptide amide as a new tyrosinase inhibitor

Abstract

AbstractTwenty two kojic acid–tripeptide amides were prepared using a solid‐phase Fmoc/tBu strategy with Rink Amide SURE® 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‐NH2 proved to be the best compound, with the highest inhibitory activity, which was maintained over different storage times under various temperatures and pHs. © 2007 Wiley Periodicals, Inc. Biopolymers (Pept Sci) 88: 300–307, 2007.This article was originally published online as an accepted preprint. The ‘Published Online’ date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com