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Highly Stable Double‐Stranded DNA Containing Sequential Silver(I)‐Mediated 7‐Deazaadenine/Thymine Watson–Crick Base Pairs
Author(s) -
SantamaríaDíaz Noelia,
MéndezArriaga José M.,
Salas Juan M.,
Galindo Miguel A.
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600924
Subject(s) - chemistry , base pair , thymine , nucleobase , oligonucleotide , crystallography , dna , hydrogen bond , circular dichroism , molecular structure of nucleic acids: a structure for deoxyribose nucleic acid , stereochemistry , duplex (building) , molecule , biochemistry , organic chemistry
The oligonucleotide d(TX) 9 , which consists of an octadecamer sequence with alternating non‐canonical 7‐deazaadenine (X) and canonical thymine (T) as the nucleobases, was synthesized and shown to hybridize into double‐stranded DNA through the formation of hydrogen‐bonded Watson–Crick base pairs. dsDNA with metal‐mediated base pairs was then obtained by selectively replacing W‐C hydrogen bonds by coordination bonds to central silver(I) ions. The oligonucleotide I adopts a duplex structure in the absence of Ag + ions, and its stability is significantly enhanced in the presence of Ag + ions while its double‐helix structure is retained. Temperature‐dependent UV spectroscopy, circular dichroism spectroscopy, and ESI mass spectrometry were used to confirm the selective formation of the silver(I)‐mediated base pairs. This strategy could become useful for preparing stable metallo‐DNA‐based nanostructures.