Localized and regulated peptide pigment formation inside liquid droplets through confined enzymatic oxidation

Kenny Barriales; Salma Kassem; Deborah Sementa; Alfredo Vidal Ceballos; Tong Wang; Shadman Khandaker; Rinat R. Abzalimov; Ankit Jain; Shana Elbaum-Garfinkle; Rein V. Ulijn

doi:10.1039/D3CC04231F

Localized and regulated peptide pigment formation inside liquid droplets through confined enzymatic oxidation†

Kenny Barriales,^abc Salma Kassem,^a Deborah Sementa,^a Alfredo Vidal Ceballos,^acf Tong Wang,

^a Shadman Khandaker,^a Rinat R. Abzalimov,^a Ankit Jain,^cdef Shana Elbaum-Garfinkle^acf and Rein V. Ulijn

*^abcf

Author affiliations

* Corresponding authors

^a Advanced Science Research Center (ASRC) at the Graduate Center, City University of New York (CUNY), 85 St Nicholas Terrace, New York, New York 10031, USA
E-mail: rulijn@gc.cuny.edu

^b Department of Chemistry, Hunter College, City University of New York, 695 Park Avenue, New York, New York 10065, USA

^c Ph.D. Program in Chemistry, The Graduate Center of the City University of New York, New York, New York 10016, USA

^d Department of Chemistry and Biochemistry, Brooklyn College, City University of New York, 2900 Bedford Avenue, Brooklyn, NY 11210, USA

^e Brooklyn College Cancer Center, Brooklyn College, The City University of New York, 2900 Beford Ave, Brooklyn, NY 11210, USA

^f Ph.D. Program in Biochemistry, The Graduate Center of the City University of New York, New York, New York, USA

Abstract

Melanin pigments are found in most life forms, where they are responsible for coloration and ultraviolet (UV) light protection. Natural melanin is a poorly soluble and complex biosynthesis product produced through confined and templated enzymatic oxidation of tyrosine. It has been challenging to create water-soluble synthetic mimics. This study demonstrates the enzymatic synthesis of oxidized phenols confined inside liquid droplets. We use an amphiphilic, bifunctional peptide, DYFR₉, that combines a tyrosine tripeptide previously shown to undergo enzymatic oxidation to form peptide pigments with broad absorbance, and polyarginine to facilitate complex coacervation in the presence of ATP. When ATP, DYFR₉ are mixed and exposed to tyrosinase, pigmented liquid droplets result, while no appreciable oxidation is observed in the bulk.

This article is part of the themed collection: Celebrating the 70th Birthday and Achievements of David Lynn

Chemical Communications

Localized and regulated peptide pigment formation inside liquid droplets through confined enzymatic oxidation†

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Localized and regulated peptide pigment formation inside liquid droplets through confined enzymatic oxidation

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