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Induced α,γ‐cyclic peptide rotodimer recognition by nucleobase scaffolds
Author(s) -
Panciera Michele,
GonzálezFreire Eva,
Calvelo Martín,
Amorín Manuel,
Granja Juan R.
Publication year - 2020
Publication title -
peptide science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.533
H-Index - 7
ISSN - 2475-8817
DOI - 10.1002/pep2.24132
Subject(s) - peptide , nucleobase , side chain , oligonucleotide , dimer , cyclic peptide , stacking , chemistry , peptide nucleic acid , hydrogen bond , supramolecular chemistry , crystallography , combinatorial chemistry , biophysics , stereochemistry , molecule , biochemistry , dna , biology , polymer , organic chemistry , crystal structure
The β‐sheet‐type structures derived from the stacking of α,γ‐cyclic peptides to form peptides nanotubes can provide different topoisomers, nonequivalent cyclic peptide stacks generated by the relative rotation through the channel axis of one cyclic peptide with respect to the next component. This rotation generates a series of cyclic peptide dimers paired by the same type of hydrogen bond pattern but differentiated by the cross‐strand side chain‐side chain pairwise. The control of this peptide‐peptide relative orientation in stacked supramolecular aggregates is required for practical applications in material sciences, sensing, or biology. We propose the use of small oligonucleotides to control the prevalence of a particular dimer through the formation of specific hydrogen bonds between cyclic peptides bearing a nucleobase attached to a serine side chain with a complementary oligonucleotide (peptide nucleic acid).