Jump to main content
Jump to site search


Melanin production by tyrosinase activity on a tyrosine-rich peptide fragment and pH-dependent self-assembly of its lipidated analogue

Author affiliations

Abstract

We investigate the self-assembly of a palmitoylated (C16-chain at the N terminus) peptide fragment in comparison to the unlipidated peptide EELNRYY, a fragment of the gut hormone peptide PYY3–36. The lipopeptide C16-EELNRYY shows remarkable pH-dependent self-assembly above measured critical aggregation concentrations, forming fibrils at pH 7, but micelles at pH 10. The parent peptide does not show self-assembly behaviour. The lipopeptide forms hydrogels at sufficiently high concentration at pH 7, the dynamic mechanical properties of which were measured. We also show that the tyrosine functionality at the C terminus of EELNRYY can be used to enzymatically produce the pigment melanin. The enzyme tyrosinase oxidises tyrosine into 3,4-dihydroxyphenylalanine (DOPA), DOPA-quinone and further products, eventually forming eumelanin. This is a mechanism of photo-protection in the skin, for this reason controlling tyrosinase activity is a major target for skin care applications and EELNRYY has potential to be developed for such uses.

Graphical abstract: Melanin production by tyrosinase activity on a tyrosine-rich peptide fragment and pH-dependent self-assembly of its lipidated analogue

Back to tab navigation

Supplementary files

Publication details

The article was received on 07 Mar 2019, accepted on 15 Apr 2019 and first published on 15 Apr 2019


Article type: Paper
DOI: 10.1039/C9OB00550A
Citation: Org. Biomol. Chem., 2019, Advance Article

  •   Request permissions

    Melanin production by tyrosinase activity on a tyrosine-rich peptide fragment and pH-dependent self-assembly of its lipidated analogue

    J. A. Hutchinson, I. W. Hamley, C. J. C. Edwards-Gayle, V. Castelletto, C. Piras, R. Cramer, R. Kowalczyk, J. Seitsonen, J. Ruokolainen and R. P. Rambo, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB00550A

Search articles by author

Spotlight

Advertisements