Polymeric peptide pigments with sequence-encoded properties

Ayala Lampel; Scott A McPhee; Hang-Ah Park; Gary G Scott; Sunita Humagain; Doeke R Hekstra; Barney Yoo; Pim W J M Frederix; Tai-De Li; Rinat R Abzalimov; Steven G Greenbaum; Tell Tuttle; Chunhua Hu; Christopher J Bettinger; Rein V Ulijn

doi:10.1126/science.aal5005

Polymeric peptide pigments with sequence-encoded properties

Science. 2017 Jun 9;356(6342):1064-1068. doi: 10.1126/science.aal5005.

Authors

Ayala Lampel¹, Scott A McPhee¹, Hang-Ah Park², Gary G Scott³, Sunita Humagain^{4

5}, Doeke R Hekstra⁶, Barney Yoo⁷, Pim W J M Frederix⁸, Tai-De Li¹, Rinat R Abzalimov¹, Steven G Greenbaum^{4

5}, Tell Tuttle³, Chunhua Hu⁹, Christopher J Bettinger^{2

10

11}, Rein V Ulijn^{12

5

7}

Affiliations

¹ Advanced Science Research Center at the Graduate Center of the City University of New York, 85 Saint Nicholas Terrace, New York, NY 10031, USA.
² Department of Materials Science and Engineering, Carnegie Mellon University, 5000 Forbes Avenue, Pittsburgh, PA 15213, USA.
³ WestCHEM and Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, UK.
⁴ Department of Physics and Astronomy, Hunter College, City University of New York, 695 Park Avenue, New York, NY 10065, USA.
⁵ Ph.D. programs in Biochemistry, Chemistry and Physics, The Graduate Center of the City University of New York, NY 10016, USA.
⁶ Department of Molecular and Cellular Biology, School of Engineering and Applied Sciences, FAS Center for Systems Biology, Harvard University, Cambridge, MA 02138, USA.
⁷ Department of Chemistry, Hunter College, City University of New York, 695 Park Avenue, New York, NY 10065, USA.
⁸ Groningen Biomolecular Sciences and Biotechnology Institute, Rijksuniversiteit Groningen, Groningen, Netherlands.
⁹ Department of Chemistry, Silver Center for Arts and Science, 100 Washington Square East, New York University, New York, NY 10003, USA.
¹⁰ Department of Biomedical Engineering, Carnegie Mellon University, 5000 Forbes Avenue, Pittsburgh, PA 15213, USA.
¹¹ McGowan Institute of Regenerative Medicine, 450 Technology Drive, Suite 300, Pittsburgh, PA 15219, USA.
¹² Advanced Science Research Center at the Graduate Center of the City University of New York, 85 Saint Nicholas Terrace, New York, NY 10031, USA. rein.ulijn@asrc.cuny.edu.

PMID: 28596363
DOI: 10.1126/science.aal5005

Abstract

Melanins are a family of heterogeneous polymeric pigments that provide ultraviolet (UV) light protection, structural support, coloration, and free radical scavenging. Formed by oxidative oligomerization of catecholic small molecules, the physical properties of melanins are influenced by covalent and noncovalent disorder. We report the use of tyrosine-containing tripeptides as tunable precursors for polymeric pigments. In these structures, phenols are presented in a (supra-)molecular context dictated by the positions of the amino acids in the peptide sequence. Oxidative polymerization can be tuned in a sequence-dependent manner, resulting in peptide sequence-encoded properties such as UV absorbance, morphology, coloration, and electrochemical properties over a considerable range. Short peptides have low barriers to application and can be easily scaled, suggesting near-term applications in cosmetics and biomedicine.

Publication types

Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Chromatography, High Pressure Liquid
Mass Spectrometry
Melanins / chemistry*
Oxidation-Reduction
Peptides / chemistry*
Protein Conformation
Protein Multimerization
Tyrosine / chemistry
Ultraviolet Rays

Substances

Melanins
Peptides
Tyrosine