Searching for the ideal triazole: Investigating the 1,5-triazole as a charge neutral DNA backbone mimic

Ysobel R. Baker, Diallo Traoré, Przemyslaw Wanat, Agnès Tyburn, Afaf H. El-Sagheer, TomBrown. Tetrahedron 76 (7), 130914, 2020.


A novel triazole linkage that mimics the phosphodiester backbone in DNA was designed, synthesised and evaluated. Unlike previous work which utilised copper to form a 1,4 triazole linkage in the DNA backbone, a ruthenium catalyst was used to yield a 1,5 triazole. The artificial linkage was incorporated into a DNA backbone via a phosphoramidite building block using solid phase synthesis. The biophysical properties of DNA with a 1,5 triazole linkage in the backbone were evaluated by UV melting and circular dichroism and compared to DNA modified with previously reported 1,4 triazole linkages of various lengths.