Journal Article

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

Kumar, Mohit, Ulijn, Rein V, Ing, Nicole L, Hochbaum, Allon I, Narang, Vishal, Wijerathne, Nadeesha K

2018

Overview

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.

• Publisher: Nature Publishing Group
• Subject: Amino acids / Assembling / Chymotrypsin / Coding / Core wire / Diimide / Energy harvesting / Environmental cleanup / Esters / Molecular chains / Naphthalene / Organic chemistry / Self-assembly / Tyrosine