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Cover Feature: Synthetic, Structural, and RNA Binding Studies on 2‐Aminopyridine‐Modified Triplex‐Forming Peptide Nucleic Acids (Chem. Eur. J. 17/2019)
Author(s) -
Kotikam Venubabu,
Kennedy Scott D.,
MacKay James A.,
Rozners Eriks
Publication year - 2019
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201900719
Subject(s) - nucleobase , peptide nucleic acid , chemistry , nucleic acid , steric effects , rna , peptide , stereochemistry , nucleic acid structure , crystallography , combinatorial chemistry , dna , biochemistry , gene
Biophysical and NMR‐structural studies uncover an unexpected interplay of electronic and structural properties of nucleobase modifications in triple helices formed by peptide nucleic acid (PNA) and double‐stranded RNA. Contrary to expectations, modification of 2‐aminopyridine nucleobase with the electron‐donating 4‐methoxy group did not stabilize the triplex. The cover picture shows the first NMR structure of a PNA–RNA triplex. Steric and electronic repulsion between the oxygen of a 4‐methyxy group and the oxygen of the carbonyl connecting the adjacent PNA nucleobase to the PNA backbone is identified (note red spheres) as the likely cause of triplex destabilization. More information can be found in the Full Paper by E. Rozners et al. on page 4367.