Fluorobenzene Nucleobase Analogues for Triplex-Forming Peptide Nucleic Acids.
RNA recognition
fluorinated nucleobases
non-canonical hydrogen bonding
peptide nucleic acids
triple helixes
Journal
Chembiochem : a European journal of chemical biology
ISSN: 1439-7633
Titre abrégé: Chembiochem
Pays: Germany
ID NLM: 100937360
Informations de publication
Date de publication:
04 02 2022
04 02 2022
Historique:
revised:
24
11
2021
received:
16
10
2021
pubmed:
11
12
2021
medline:
9
3
2022
entrez:
10
12
2021
Statut:
ppublish
Résumé
2,4-Difluorotoluene is a nonpolar isostere of thymidine that has been used as a powerful mechanistic probe to study the role of hydrogen bonding in nucleic acid recognition and interactions with polymerases. In the present study, we evaluated five fluorinated benzenes as nucleobase analogues in peptide nucleic acids designed for triple helical recognition of double helical RNA. We found that analogues having para and ortho fluorine substitution patterns (as in 2,4-difluorotoluene) selectively stabilized Hoogsteen triplets with U-A base pairs. The results were consistent with attractive electrostatic interactions akin to non-canonical F to H-N and C-H to N hydrogen bonding. The fluorinated nucleobases were not able to stabilize Hoogsteen-like triplets with pyrimidines in either G-C or A-U base pairs. Our results illustrate the ability of fluorine to engage in non-canonical base pairing and provide insights into triple helical recognition of RNA.
Identifiants
pubmed: 34889020
doi: 10.1002/cbic.202100560
pmc: PMC8935525
mid: NIHMS1784515
doi:
Substances chimiques
Fluorobenzenes
0
Peptide Nucleic Acids
0
RNA
63231-63-0
Types de publication
Journal Article
Research Support, N.I.H., Extramural
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202100560Subventions
Organisme : NIGMS NIH HHS
ID : R35 GM130207
Pays : United States
Informations de copyright
© 2021 Wiley-VCH GmbH.
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