Cross-linked DNA: site-selective "click" ligation in duplexes with bis-azides and stability changes caused by internal cross-links

Bioconjugate Chemistry
Hai Xiong, Frank Seela

Abstract

Heterodimeric interstrand cross-linked DNA was constructed by the "bis-click" reaction carried out on preformed oligonucleotide duplexes with the bis-azide 1. For this, alkynylated 8-aza-7-deazapurine or corresponding 5-substituted pyrimidine nucleosides were synthesized. Cross-linking resulted in chemoselective formation of heterodimeric duplexes while homodimers were suppressed. For product identification, heterodimeric DNA was prepared by the "stepwise click" reaction, while noncomplementary homodimers were accessible by "bis-click" chemistry, unequivocally. Studies on duplex melting of complementary cross-linked duplexes (heterodimers) revealed significantly increased Tm values compared to the non-cross-linked congeners. The stability of this cross-linked DNA depends on the linker length and the site of modification. Cross-linked homodimers hybridized with single-stranded complementary oligonucleotides show much lower stability.

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Citations

Aug 27, 2014·Organic Letters·Maksim A FomichVadim V Shmanai
Mar 8, 2017·Bioorganic & Medicinal Chemistry·Kazumitsu OnizukaFumi Nagatsugi
Oct 30, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tim EfthymiouJean-Paul Desaulniers
Dec 21, 2013·Organic & Biomolecular Chemistry·L L G CarretteA Madder
Jan 15, 2021·Chemical Reviews·Nicolò Zuin FantoniTom Brown

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