Chemical Architecture and Applications of Nucleic Acid Derivatives Containing 1,2,3-Triazole Functionalities Synthesized via Click Chemistry

Abstract

There is considerable attention directed at chemically modifying nucleic acids with robust functional groups in order to alter their properties. Since the breakthrough of copper-assisted azide-alkyne cycloadditions (CuAAC), there have been several reports describing the synthesis and properties of novel triazole-modified nucleic acid derivatives for potential downstream DNA- and RNA-based applications. This review will focus on highlighting representative novel nucleic acid molecular structures that have been synthesized via the “click” azide-alkyne cycloaddition. Many of these derivatives show compatibility for various applications that involve enzymatic transformation, nucleic acid hybridization, molecular tagging and purification, and gene silencing. The details of these applications are discussed. In conclusion, the future of nucleic acid analogues functionalized with triazoles is promising.

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

“…The procedure described above was followed to obtain compound 9, employing Cu(OAc) 2 (10). The procedure described above was followed to obtain compound 10, employing Cu(OAc) 2 (11). The procedure described above was followed to obtain compound 11, employing Cu(OAc) 2 (12).…”

“…Moreover, this process allows for the assembly of complex molecules, thus generating new unknown structures with an added potential biological and engineering value [8][9][10]. 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].…”

Insight Into the Inhibition of Ribonucleotide Reductases by 2'-chloro-2'-deoxynucleotides and 2'-azido-2'-deoxynucleotides: Biomimetic Studies with Model Substrates

“…Azido-modified oligonucleotides are widely used for the synthesis of bioconjugates employing azide-alkyne click chemistry approach. [81][82][83][84][85][86][87] Phosphoramidite reagents are used to introduce the terminal alkynes or cyclooctynes into the oligonucleotides. However this approach cannot be used for the azido modified compounds 88 as the azide with P (III) in the phosphoramidite undergoes Staudinger reaction with the azide.…”

“…Synthesis of oligonucleotides using phosphoramidite chemistry is generally not possible since azides are proven to be susceptible to Staudinger reduction in the presence of P (III). 86 Inspite of this finding Fauster proved that the azido group at the C2′-position of furanose are compatible to the phosphoramidite reagent with the steps of automated oligonucleotide synthesis (Scheme 14).…”

“…Synthesis of azido-modified RNA fragments using phosphoramidite chemistry. 86 Sekine et al 88 prepared 2-azidodeoxyadenosine, 56 from deoxyguanosine by using combined reagent of TMSN 3 -BuONO. Further to incorporate 56 into DNA they tried two approaches.…”