Issue 26, 2021

Rational design of a photoswitchable DNA glue enabling high regulatory function and supramolecular chirality transfer

Abstract

Short, complementary DNA single strands with mismatched base pairs cannot undergo spontaneous formation of duplex DNA (dsDNA). Mismatch binding ligands (MBLs) can compensate this effect, inducing the formation of the double helix and thereby acting as a molecular glue. Here, we present the rational design of photoswitchable MBLs that allow for reversible dsDNA assembly by light. Careful choice of the azobenzene core structure results in excellent band separation of the E and Z isomers of the involved chromophores. This effect allows for efficient use of light as an external control element for duplex DNA formation and for an in-depth study of the DNA–ligand interaction by UV-Vis, SPR, and CD spectroscopy, revealing a tight mutual interaction and complementarity between the photoswitchable ligand and the mismatched DNA. We also show that the configuration of the switch reversibly dictates the conformation of the DNA strands, while the dsDNA serves as a chiral clamp and translates its chiral information onto the ligand inducing a preference in helical chirality of the Z isomer of the MBLs.

Graphical abstract: Rational design of a photoswitchable DNA glue enabling high regulatory function and supramolecular chirality transfer

Supplementary files

Article information

Article type
Edge Article
Submitted
20 Apr. 2021
Accepted
22 Maijs 2021
First published
27 Maijs 2021
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2021,12, 9207-9220

Rational design of a photoswitchable DNA glue enabling high regulatory function and supramolecular chirality transfer

N. A. Simeth, S. Kobayashi, P. Kobauri, S. Crespi, W. Szymanski, K. Nakatani, C. Dohno and B. L. Feringa, Chem. Sci., 2021, 12, 9207 DOI: 10.1039/D1SC02194J

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