Xylo-Configured oligonucleotides (XNA, xylo nucleic acid): synthesis of conformationally restricted derivatives and hybridization towards DNA and RNA complements

Solution Structure and Conformational Dynamics of Deoxyxylonucleic Acids (dXNA): An Orthogonal Nucleic Acid Candidate

“…So far, only limited literature data are available for the cross pairing of dXNA with RNA. [13,14] From a structural point of view, it would be important to further investigate the inherent flexibility of the dXNA backbone by designing a suitable selfcomplementary sequence and studying the formation of a hairpin form.…”

“…[12] Research into dXNA and locked dXNA [13,14] was performed by Seela et al [11,[15][16][17][18][19] and Wengel et al [13,14] mainly in the context of the antigene and antisense strategies. They synthesized deoxyxylo-derived nucleotide building blocks and their corresponding oligonucleotides to study their nuclease stability and conformational and hybridization properties with themselves and with complementary DNA [11,[15][16][17][18][19] and RNA.…”

“…They synthesized deoxyxylo-derived nucleotide building blocks and their corresponding oligonucleotides to study their nuclease stability and conformational and hybridization properties with themselves and with complementary DNA [11,[15][16][17][18][19] and RNA. [13,14] It was observed that dXNAs are resistant to degradation by cellular nucleases. Notably, it was observed that the introduction of a few deoxyxylo residues in one strand of DNA [11,15,17] or RNA [13,14] significantly reduced the thermal stability of the double-stranded heteroduplexes, whereas complete modification of one strand abolished duplex stability.…”

“…[13,14] It was observed that dXNAs are resistant to degradation by cellular nucleases. Notably, it was observed that the introduction of a few deoxyxylo residues in one strand of DNA [11,15,17] or RNA [13,14] significantly reduced the thermal stability of the double-stranded heteroduplexes, whereas complete modification of one strand abolished duplex stability. [11] However, it was found that selfcomplementary fully modified dXNA can form duplexes [11] with at least similar stabilities to DNA duplexes.…”

Cytotoxic and Mutagenic Properties of C3′-Epimeric Lesions of 2′-Deoxyribonucleosides in Escherichia coli Cells

“…14–21 Indeed, the thermal stability of the duplexes was substantially diminished upon the introduction of a few xylose nucleosides into one strand of DNA 14–17 or RNA; 20,21 however, complete modification of one strand abrogated duplex formation. 14–17 Interestingly, duplexes formed from self-complementary fully modified xylose-DNA (dXNA) exhibit stabilities similar to or even greater than those of the corresponding DNA duplexes.…”