ArticleThe Journal of organic chemistry2010
Azide-tetrazole equilibrium of C-6 azidopurine nucleosides and their ligation reactions with alkynes.
Article in The Journal of organic chemistry, 2010. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 20 papers.
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Who cites it
20 citing papers in PubMed.
- Preparation of 6-Azido-2-Chloropurine-2'-Deoxyriboside by Enzymatic Transglycosylation Reaction Catalyzed by Lactobacillus leichmannii Type II Nucleoside Deoxyribosyltransferase.Doklady. Biochemistry and biophysics · 2025Article
- Synthesis of Ethynyl Trifluoromethyl Sulfide and Its Application to the Synthesis of CFMolecules (Basel, Switzerland) · 2025Article
- Synthesis of Indole Derivatives via Aryl Triazole Ring-Opening and Subsequent Cyclization.Molecules (Basel, Switzerland) · 2025Article
- Nitrogen-Centered Radicals Derived from Azidonucleosides.Molecules (Basel, Switzerland) · 2024Review
- Comparative Analysis of Enzymatic Transglycosylation Using E. coli Nucleoside Phosphorylases: A Synthetic Concept for the Preparation of Purine Modified 2′-Deoxyribonucleosides from RibonucleosidesInternational journal of molecular sciences · 2022Article
- Scope of tetrazolo[1,5-Beilstein journal of organic chemistry · 2022Article
- Novel Bis- and Mono-Pyrrolo[2,3-Molecules (Basel, Switzerland) · 2021Article
- Synthesis and Evaluations of "1,4-Triazolyl Combretacoumarins" and Desmethoxy Analogues.European journal of organic chemistry · 2019Article
- Facile functionalization at the C4 position of pyrimidine nucleosides via amide group activation with (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (BOP) and biological evaluations of the products.Organic & biomolecular chemistry · 2017Article
- A novel bis(pinacolato)diboron-mediated N-O bond deoxygenative route to C6 benzotriazolyl purine nucleoside derivatives.Organic & biomolecular chemistry · 2016Article
- Ruthenium-Catalyzed C-H Bond Activation Approach to Azolyl Aminals and Hemiaminal Ethers, Mechanistic Evaluations, and Isomer Interconversion.ACS catalysis · 2016Article
- Diarylmethanes through an Unprecedented Palladium-Catalyzed C-C Cross-Coupling of 1-(Aryl)methoxy-1ChemCatChem · 2015Article
- Structure-activity relationship studies of QS11, a small molecule Wnt synergistic agonist.Bioorganic & medicinal chemistry letters · 2015Article
- Cladribine Analogues via O⁶-(Benzotriazolyl) Derivatives of Guanine Nucleosides.Molecules (Basel, Switzerland) · 2015Article
- The "Speedy" Synthesis of Atom-Specific (15)N Imino/Amido-Labeled RNA.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
- Triazole-containing monophosphate mRNA cap analogs as effective translation inhibitors.RNA (New York, N.Y.) · 2014Article
- Chemical architecture and applications of nucleic acid derivatives containing 1,2,3-triazole functionalities synthesized via click chemistry.Molecules (Basel, Switzerland) · 2012Review
- Synthesis of deuterated 1,2,3-triazoles.The Journal of organic chemistry · 2012Article
- Synthesis and biological properties of C-2 triazolylinosine derivatives.The Journal of organic chemistry · 2012Article
- Fused tetrazoles as azide surrogates in click reaction: efficient synthesis of N-heterocycle-substituted 1,2,3-triazoles.Organic letters · 2010Article
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5 authors.
Funding
Abstract
Facile syntheses of C-6 azidopurine ribonucleosides and 2'-deoxyribonucleosides have been developed. For silyl- and acetyl-protected as well as unprotected nucleosides, access to the azido derivatives could be readily attained via displacement of BtO(-) from the O(6)-(benzotriazol-1-yl)inosine nucleosides by azide anion. Use of diphenylphosphoryl azide/DBU as a simple route to the acetyl-protected azido nucleosides was also evaluated, but this proved to be inferior. Since these azido nucleosides can exist in an azide.tetrazole equilibrium, the effect of solvent polarity on this equilibrium was investigated. Subsequently, a detailed analysis of Cu-mediated azide-alkyne ("click") ligation was undertaken. Biphasic CH(2)Cl(2)/H(2)O medium proved to be best for the ligation reactions, suppressing the undesired azide reduction that was competing. Interestingly, although the tetrazolyl isomer predominates (ca. 80%) in CD(2)Cl(2) and in CD(2)Cl(2)/D(2)O, the Cu-catalyzed click reactions proceed smoothly with the silyl-protected ribo- and 2'-deoxyribonucleosides, leading to the C-6 triazolyl products in good to excellent yields. Thus, depletion of the azido form from the reaction mixture shifts the azide.tetrazole equilibrium, eventually resulting in complete consumption of azide and tetrazole. In several cases, major and minor azide-alkyne ligation products were observed, and characterization data are provided for both. In order to confirm the regiochemistry leading to the major isomer, one product was crystallized and evaluated by X-ray crystallography. The Cu-catalyzed azide-alkyne ligation is clearly efficient and significantly superior to thermal reactions, which were slow. Biological evaluation showed low cytotoxicities for the agents, suggesting their usefulness as biological probes.
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