The synthesis of double-headed nucleosides by the CuAAC reaction and their effect in secondary nucleic acid structures

Abstract

Four double-headed nucleosides were prepared by the CuAAC reaction. Hereby, a triazole-containing linker connects an additional thymine or adenine to the 2'-position of 2'-deoxyuridine, a thymine to the 5'-position of thymidine and a thymine to the 6'-position of an LNA-thymidine monomer. Whereas no conclusive recognition effects of the additional thymines were found when introduced in LNA or at the 5'-position, both thymine and adenine in the 2'-position were found to stabilise three-way junctions in both dsDNA and DNA : RNA contexts and to give cross-strand interactions in a DNA-duplex, when specifically introduced in a so-called (+1)-zipper motif.

C2′-Pyrene-Functionalized Triazole-Linked DNA: Universal DNA/RNA Hybridization Probes

“…18–20 Moreover, monomers W - Z were selected to study the influence of the linker between the pyrene and triazole moieties on hybridization properties of correspondingly modified ONs, while non-functionalized monomer V provides insight into the relative roles of pyrene and triazole moieties. Recent reports have described pre- 25,26 and post-synthetic 6e,27 uses of the CuAAC reaction for 2′-functionalization of nucleotides. However, the present work is the first example of ONs modified with monomers where pyrene-functionalized 1,2,3-triazolyl moieties are directly attached to the 2′-position of nucleosides.…”

Multicomponent Click Synthesis of New 1,2,3-Triazole Derivatives of Pyrimidine Nucleobases: Promising Acidic Corrosion Inhibitors for Steel

“…Monopropargyl pyrimidine nucleobases (uracil and thymine) are versatile building blocks for the synthesis of biologically relevant 1,2,3-triazoles [11]. They are generally used as starting material for the synthesis of triazole nucleosides [12][13][14][15][16][17][18][19], triazole nucleotides [20][21][22][23], oxiconazole analogues [24], nucleopeptides [25], inhibitors of human topoisomerase type II [26], and nucleoamino oxyacids [27]. Further, these propargyl nucleobases are also used in the synthesis of organogels [28], and as corrosion inhibitors [29].…”

Double-headed nucleotides in DNA-zipper structures; base–base interactions and UV-induced cross-coupling in the minor groove

“…1, T tPh /T tU /T tT and T 4t /T 1t , respectively). 8,9 However, no zipper interactions with similar specificity were found all though T tU demonstrated a strong tendency to form binding to the floor of the minor groove. 8 Herein, we investigate the replacement of the additional thymine of nucleotide T T with the other nucleobases cytosine and adenine (nucleotide monomers T C and T A ), in order to explore the possibility of various base-base interactions in the minor groove and to compare with the strong thyminethymine and thymine-phenyl stacking interactions previously found in the (23) zipper constructs.…”

“…[1][2][3] Recently, we and others have focused on interactions either at the duplex surface or in the duplex core by the introduction of double-headed or double-functionalized nucleotides into the duplex. [4][5][6][7][8][9][10][11][12][13] As an example, a doubleheaded nucleotide with an additional thymine nucleobase positioned in the 59(S)-position trough a methylene linker has been investigated. 5 Each incorporation of this modification (termed T T in Fig.…”