79953-03-0Relevant articles and documents
Self-Assembly of Functionalized Lipophilic Guanosines into Cation-Free Stacked Guanine-Quartets
Campitiello, Marilena,Cremonini, Alessio,Squillaci, Marco A.,Pieraccini, Silvia,Ciesielski, Artur,Samorì, Paolo,Masiero, Stefano
, p. 9970 - 9978 (2021/07/31)
The hierarchical self-assembly of various lipophilic guanosines exposing either a phenyl or a ferrocenyl group in the C(8) position was investigated. In a solution, all the derivatives were found to self-assemble primarily into isolated guanine (G)-quartets. In spite of the apparent similar bulkiness of the two substituents, most of the derivatives form disordered structures in the solid state, whereas a specific 8-phenyl derivative self-assembles into an unprecedented, cation-free stacked G-quartet architecture.
Pd(0)/Cu(I)-mediated direct arylation of 2′-deoxyadenosines: Mechanistic role of Cu(I) and reactivity comparisons with related purine nucleosides
Storr, Thomas E.,Baumann, Christoph G.,Thatcher, Robert J.,De Ornellas, Sara,Whitwood, Adrian C.,Fairlamb, Ian J. S.
supporting information; experimental part, p. 5810 - 5821 (2009/12/26)
(Chemical Equation Presented) Pd/Cu-mediated direct arylation of 2′-deoxyadenosine with various aryl iodides provides 8-arylated 2′-deoxyadenosine derivatives in good yields. Following significant reaction optimization, it has been determined that a subst
A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs)
Collier, Alice,Wagner, Gerd
, p. 4526 - 4532 (2008/09/19)
We report a simple and high-yielding two-step procedure for the preparation of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs). The key step of our synthesis is the Suzuki-Miyaura coupling of unprotected 8-bromo GMP and 8-bromo GTP with various
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.
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.
Reactions of Benzenediazonium Ions with Guanine and Its Derivatives
Hung, Ming-Hong,Stock, Leon M.
, p. 448 - 453 (2007/10/02)
Guanine reacts with several benzenediazonium ions rapidly in aqueous solution at pH 10.5 to form 8-(arylazo)guanines in good yield.The reaction of guanine with 4-bromobenzenediazonium ion forms ε-guanine about 50-fold more rapidly than the reaction of adenine with this ion to yield 6-purine under these experimental conditions.Guanosine reacts much more slowly than guanine with the benzenediazonium ions in aqueous solution at pH 8.5 or 10.5 to give 8-arylguanosines.The structures of these products were established by their spectroscopic properties and by their quantitative conversion to 8-arylguanines. 5'-Guanylic acid also reacts quite slowly with the benzenediazonium ions in aqueous solution at pH 10.5.Only the compounds with strong electron-withdrawing groups yield N-2 triazenes at ambient temperature.No 8-aryl or 8-arylazo compounds are formed with 5'-guanylic acid at this temperature.However, 4-bromo- and 4-sulfobenzenediazonium ions react with 5'-guanylic acid at higher temperatures to yield the 8-aryl-5'-guanylic acids in low yield.The structures of these products were proven by hydrolysis to 8-arylguanines.The 8-arylguanosines and the 8-aryl-5'-guanylic acids are formed via free-radical phenylation reactions.The factors governing the reactivity of the adenines and the guanines are discussed.
