73340-80-4Relevant academic research and scientific papers
8-(p-CF3-cinnamyl)-modified purine nucleosides as promising fluorescent probes
Zilbershtein, Lital,Silberman, Alon,Fischer, Bilha
experimental part, p. 7763 - 7773 (2011/12/14)
Natural nucleotides are not useful as fluorescent probes because of their low quantum yields. Therefore, a common methodology for the detection of RNA and DNA is the application of extrinsic fluorescent dyes coupled to bases in oligonucleotides. To overco
Site-selective direct arylation of unprotected adenine nucleosides mediated by palladium and copper: insights into the reaction mechanism
Storr, Thomas E.,Firth, Andrew G.,Wilson, Karen,Darley, Kate,Baumann, Christoph G.,Fairlamb, Ian J.S.
, p. 6125 - 6137 (2008/09/21)
Reaction conditions facilitating the site-selective direct aryl functionalisation at the C-8 position of adenine nucleosides have been identified. Many different aromatic components may be effectively cross-coupled to provide a diverse array of arylated adenine nucleoside products without the need for ribose or adenine protecting groups. The optimal palladium catalyst loading lies between 0.5 and 5 mol %. Addition of excess mercury to the reaction had a negligible affect on catalysis, suggesting the involvement of a homogeneous catalytic species. A study by transmission electron microscopy (TEM) shows that metal containing nanoparticles, ca. 3 nm with good uniformity, are formed during the latter stages of the reaction. Stabilised PVP palladium colloids (PVP=N-polyvinylpyrrolidone) are catalytically active in the direct arylation process, releasing homogenous palladium into solution. The effect of various substituted 2-pyridine ligand additives has been investigated. A mechanism for the site-selective arylation of adenosine is proposed.
Suzuki-Miyaura cross-coupling of unprotected halopurine nucleosides in water - Influence of catalyst and cosolvent
Collier, Alice,Wagner, Gerd K.
, p. 3713 - 3721 (2007/10/03)
Reaction conditions for the Suzuki-Miyaura cross-coupling of unprotected halopurine nucleosides with arylboronic acids in aqueous media were investigated. A series of arylated purine nucleosides was prepared in water without an organic cosolvent, using either Pd(PPh3)4 or Pd(OAc)2/TPPTS as the catalyst. Copyright Taylor & Francis Group, LLC.
Synthesis of novel 2-aryl AICAR derivatives
Kohyama, Naoki,Katashima, Tomoyuki,Yamamoto, Yukio
, p. 2799 - 2804 (2007/10/03)
Novel 2-aryl AICAR (5-Amino-1-β-D-ribofuranosylimidazole-4- carboxamide) derivatives 8 were synthesized via the Suzuki-Miyaura cross-coupling reactions of 8-bromoadenosine. Following conversion of the adenine moiety of 4 to hypoxanthine (5) and the introduction of a MEM group, hydrolysis of 7 gave desired 2-aryl AICAR derivatives 8.
Efficient one-step Suzuki arylation of unprotected halonucleosides, using water-soluble palladium catalysts
Western, Elizabeth C.,Daft, Jonathan R.,Johnson II, Edward M.,Gannett, Peter M.,Shaughnessy, Kevin H.
, p. 6767 - 6774 (2007/10/03)
Modification of nucleosides to give pharmaceutically active compounds, mutagenesis models, and oligonucleotide structural probes continues to be of great interest. The aqueous-phase modification of unprotected halonucleosides is reported herein. Using a catalyst derived from tris(3-sulfonatophenyl)phosphine (TPPTS) and palladium acetate, 8-bromo-2′-deoxyguanosine (8-BrdG) is coupled with arylboronic acids to give 8-aryl-2′-deoxyguanosine adducts (8-ArdG) in excellent yield in a 2: 1 water: acetonitrile solvent mixture. The TPPTS ligand was found to be superior to water-soluble alkylphosphines for this coupling reaction. The coupling chemistry has been extended to 8-bromo-2′-deoxyadenosine (8-BrdA) and 5-iodo-2′-deoxyuridine (5-IdU), as well as the ribonucleosides 8-bromoguanosine and 8-bromoadenosine. Good to excellent yields of arylated adducts are obtained in all cases. With use of tri(4,6-dimethyl-3-sulfonatophenyl)phosphine (TXPTS), the Suzuki coupling of 8-BrdA and 5-IdU can be accomplished in less than 1 h at room temperature. This methodology represents an efficient and general method for halonucleoside arylation that does not require prior protection of the nucleoside.
