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Stabilization of Telomeric I‐Motif Structures by (2′ S )‐2′‐Deoxy‐2′‐ C ‐Methylcytidine Residues
Author(s) -
Aviñó Anna,
Dellafiore María,
Gargallo Raimundo,
González Carlos,
Iribarren Adolfo M.,
Montserrat Javier,
Eritja Ramon
Publication year - 2017
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.201700112
Subject(s) - oligonucleotide , telomere , chemistry , intramolecular force , stereochemistry , cytidine , nuclear magnetic resonance spectroscopy , nucleoside , structural motif , sequence motif , combinatorial chemistry , biochemistry , dna , enzyme
G‐quadruplexes and i‐motifs are tetraplex structures present in telomeres and the promoter regions of oncogenes. The possibility of producing nanodevices with pH‐sensitive functions has triggered interest in modified oligonucleotides with improved structural properties. We synthesized C‐rich oligonucleotides carrying conformationally restricted (2′ S )‐2′‐deoxy‐2′‐ C ‐methyl‐cytidine units. The effect of this modified nucleoside on the stability of intramolecular i‐motifs from the vertebrate telomere was investigated by UV, CD, and NMR spectroscopy. The replacement of selected positions of the C‐core with C‐modified residues induced the formation of stable intercalated tetraplexes at near‐neutral pH. This study demonstrates the possibility of enhancing the stability of the i‐motif by chemical modification.