Synthesis and properties of 2-azidodeoxyadenosine and its incorporation into oligodeoxynucleotides

Oligonucleotide Tagging for Copper-Free Click Conjugation

“…Moreover, it is clear that a phosphoramidite-based strategy for the introduction of an azide group, the complementary partner for SPAAC, is hampered by competitive Staudinger reduction of azide with P III -type reagents [27,31]. Therefore, our next aim was to develop a generic building block for internal incorporation in an ON chain, to facilitate subsequent on-support derivatization with any functional group of choice, including BCN or azide.…”

“…13 C-NMR spectra were recorded in CDCl 3 at 75 MHz on a Bruker DMX 300 spectrometer, using the central resonance of CDCl 3 (δ C 77.0) as the internal reference. 31 P NMR and 1 H-NMR spectra for 1, 2 and V were provided by NuMega Resonance Labs. Mass spectra were obtained on Applied Biosystems Voyager DE-Pro MALDI-TOF (no calibration) or JEOL AccuToF.…”

“…Most recently, Brown et al [25,26] further extended the latter approach by ON incorporation of aminoalkyl thymidine derivatives, followed by selective N-acylation with azide or cyclooctyne after cleavage from support. Alternative approaches for the preparation of azide-containing nucleotides-compromised by the incompatibility of azide with phosphoramidite chemistry-involve post-synthetic nucleophilic substitution [27][28][29] or selective diazotransfer reaction [30] or phosphonate-based coupling chemistry [31][32][33][34] However, a simple and general strategy for the on-support, automated synthesis of oligonucleotides with readily accessible building blocks, and suitable for introduction of any functional group (including cyclooctyne and azide), is still desirable.…”

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

“…[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. Therefore the H-phosphonate 89,90 and the phosphotriester [91][92][93][94] protocols are used for the synthesis of azide-modified oligonucleotides.…”

“…Reaction of 2-azidodeoxyadenosine with N,N-diisopropylphosphor amidite reagent. 88 Benign viral infections, e.g., common cold etc. Selected antiviral molecules available in the market depicted in Figure 1 are deoxyadenosine analogues e.g., didanosine (HIV), vidrabine (chemotherapy), adenosine analogs e.g., BCX4430 (Ebola), deoxycytidine analogues e.g., cytarabine (chemotherapy), lamivudine (HIV, hepatitis-B), zalcitabine (HIV), guanosine and deoxyguanosine analogues e.g., abacavir (HIV), telbivudine (hepatitis-B), zidovudine (HIV), deoxyuridine analogues e.g., idoxuridin.…”