Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 27, Issue 19, Pages 6064-6069Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202004990
Keywords
chirality; circular dichroism; conformational analysis; G-quadruplexes; helical structures
Categories
Funding
- Danish Council for Independent Research [DFF 4181-00206, 9040-00265A]
- University of Copenhagen, Engineering and Physical Sciences Research Council [EB-BB1250]
- University of Bath
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The study shows that fully conjugated racemic hetero[7]helicenes and DNA strands prone to fold into G-quadruplex structures interact and stabilize each other, enhancing certain conformations at increased temperatures.
The dynamic interplay between two types of chiral structures; fully conjugated racemic hetero[7]helicenes and DNA strands prone to fold into G-quadruplex structures is described. Both the [7]helicenes and the G-quadruplex DNA structures exist in more than one conformation in solution. We show that the structures interact with and stabilise each other, mutually amplifying and stabilising certain conformations at increased temperatures. The [7]helicene ligands L1 and L2 stabilise the parallel conformation of k-ras significantly, whereas hybrid (K+) and antiparallel (Na+) h-telo G-quadruplexes are stabilised upon conformational switching into altered G-quadruplex conformations. Both L1 and L2 induce parallel G-quadruplexes from hybrid structures (K+) and L1 induces hybrid G-quadruplexes from antiparallel conformations (Na+). Enantioselective binding of one helicene enantiomer is observed for helicene ligand L2, and VTCD melting experiments are used to estimate the racemisation barrier of the helicene.
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