Amino-acid-encoded biocatalytic self-assembly enables the formation of transient conducting nanostructures

• Published in: Nature chemistry Vol. 10; no. 7; pp. 696 - 703
• Main Authors: Kumar, Mohit, Ing, Nicole L, Narang, Vishal, Wijerathne, Nadeesha K, Hochbaum, Allon I, Ulijn, Rein V
• Format: Journal Article
• Language: English
• Published: England Nature Publishing Group 01.07.2018
• Subjects: Amino acids; Assembling; Chymotrypsin; Coding; Core wire; Diimide; Energy harvesting; Environmental cleanup; Esters; Molecular chains; Naphthalene; Organic chemistry; Self-assembly; Tyrosine
• ISSN: 1755-4330; 1755-4349
• DOI: 10.1038/s41557-018-0047-2

Aqueous compatible supramolecular materials hold promise for applications in environmental remediation, energy harvesting and biomedicine. One remaining challenge is to actively select a target structure from a multitude of possible options, in response to chemical signals, while maintaining constant, physiological conditions. Here, we demonstrate the use of amino acids to actively decorate a self-assembling core molecule in situ, thereby controlling its amphiphilicity and consequent mode of assembly. The core molecule is the organic semiconductor naphthalene diimide, functionalized with D- and L- tyrosine methyl esters as competing reactive sites. In the presence of α-chymotrypsin and a selected encoding amino acid, kinetic competition between ester hydrolysis and amidation results in covalent or non-covalent amino acid incorporation, and variable supramolecular self-assembly pathways. Taking advantage of the semiconducting nature of the naphthalene diimide core, electronic wires could be formed and subsequently degraded, giving rise to temporally regulated electro-conductivity.