5,16,17 While its cousin pheomelanin, which is prevalent in red hair and fair skin, is far less studied. 14,15 Eumelanin is well-studied as the most important factor in protection from harmful solar UV radiation. 2–13 Epidermal pigmentation in human beings is considered to be composed of two separate but biosynthetically related melanins: eumelanin and pheomelanin. 1 Found across different kingdoms of life, melanins have a myriad of important functions, including coloration, camouflage, thermal regulation, photoprotection, and radioprotection. Introduction Melanin is an important class of polymeric biological pigment derived mainly from amino acid precursors. With a good synthetic biomimetic material in hand, we describe cation-π interactions as an important driving force for pheomelanogenesis, further advancing our fundamental understanding of this important biological pigment.
This synthetic pheomelanin closely mimics the structure of natural pheomelanin as determined by parallel characterization of pheomelanin extracted from multiple biological sources. The resulting biomimetic and natural pheomelanins were compared via various techniques, including solid-state Nuclear Magnetic Resonance (ssNMR) and Electron Paramagnetic Resonance (EPR). Among them, the route employing 5-cysteinyl-dihydroxyphenylalanine (5-CD) as a monomer was verified as a close analogue of extracted pheomelanin from humans and birds. Three different oxidative polymerization routes were attempted to generate synthetic pheomelanin, each giving rise to structurally dissimilar materials. Herein, we investigate synthetic routes to a close mimic of natural pheomelanin.
E-mail: b Department of Materials Science and Engineering, Northwestern University, Evanston, Illinois 60208, USA c Department of Biomedical Engineering, Department of Pharmacology, International Institute for Nanotechnology, Simpson-Querrey Institute, Chemistry of Life Processes Institute, Lurie Cancer Center, Northwestern University, Evanston, Illinois 60208, USA d Institute for Sustainability and Energy at Northwestern University, Evanston, Illinois 60208, USA e Department of Chemistry & Biochemistry, University of California, San Diego, La Jolla, California 92093, USA f Evolution and Optics of Nanostructures Group, Department of Biology, The University of Ghent, 9000, Ghent, Belgium g Department of Chemistry and Chemical & Biomedical Engineering, Tagliatela College of Engineering, University of New Haven, West Haven, Connecticut 06516, USA * abce a Department of Chemistry, Northwestern University, Evanston, Illinois 60208, USA. Sci., 2023, 14, 4183-4192 Biomimetic pheomelanin to unravel the electronic, molecular and supramolecular structure of the natural product †
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