Ferrocene-modified pyrimidine nucleosides: synthesis, structure and electrochemistry.
نویسندگان
چکیده
This paper reports syntheses, crystal structures and electrochemical results for two ferrocene(Fc)-modified pyrimidine nucleosides that could potentially be used for investigating electron transfer in DNA. Fc was directly attached to the 5-position of deoxyuridine and deoxycytidine via the Stille coupling reaction. Fc-modified uridine was incorporated into DNA trinucleotides with standard solid-phase synthesis. The structures of corresponding detritylated compounds were determined by single-crystal X-ray analysis. Electrochemical investigations of all compounds by cyclic voltammetry revealed reversible redox processes.
منابع مشابه
2'-Ribose-ferrocene oligonucleotides for electronic detection of nucleic acids.
We have synthesized two novel phosphoramidites with a ferrocenyl moiety at the 2'-ribose position linked through a butoxy linker. Using automated DNA/RNA synthesis techniques, oligonucleotides containing ferrocene at various positions were prepared and characterized by HPLC, MALDI-TOF mass spectrometry, and electrochemistry. Thermal stability studies of the ferrocene-modified DNA duplexes revea...
متن کاملAn Efficient Protocol for the Synthesis of Carboacyclic Nucleosides via Aza-Conjugate Addition Reaction
A new efficient method for the synthesis of carboacyclic nucleosides as biologically interesting compounds via aza-conjugate addition of pyrimidine nucleobases to a,β-unsaturated esters in the presence of catalytic amount of LiOH.H2O (1.2-4.8 mol%) under microwave irradiation is described. This method affords the title compounds in good to excellent yields and i...
متن کاملRuthenium(II) complexes with ferrocene-modified arene ligands: synthesis and electrochemistry
A series of arene–ruthenium complexes of the general formula [RuCl2{g-C6H5(CH2)2R}L] with R1⁄4OH, CH2OH, OC(O)Fc, CH2OC(O)Fc (Fc1⁄4 ferrocenyl) and L1⁄4PPh3, (diphenylphosphino)ferrocene, or bridging 1,10-bis(diphenylphosphino)ferrocene, have been synthesized. Two synthetic pathways have been used for these ferrocene-modified arene–ruthenium complexes: (a) esterification of ferrocene carboxylic...
متن کاملSynthesis and structure of novel conformationally constrained 1',2'-azetidine-fused bicyclic pyrimidine nucleosides: their incorporation into oligo-DNAs and thermal stability of the heteroduplexes.
[structures: see text] The synthesis of novel 1',2'-aminomethylene bridged (6-aza-2-oxabicyclo[3.2.0]heptane) "azetidine" pyrimidine nucleosides and their transformations to the corresponding phosphoramidite building blocks (20, 39, and 42) for automated solid-phase oligonucleotide synthesis is reported. The novel bicyclonucleoside "azetidine" monomers were synthesized by two different strategi...
متن کاملRole of palladium in the redox electrochemistry of ferrocene monocarboxylic acid encapsulated within ORMOSIL networks.
We report herein the effect of palladium on the redox electrochemistry of ferrocene monocarboxylic acid encapsulated within an organically modified sol-gel glass network (ORMOSIL). It has been found that amount of palladium and its geometrical distribution significantly alter the redox electrochemistry of FcMCA. The geometrical distribution of palladium has been controlled by two methods: (i) p...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
عنوان ژورنال:
- Dalton transactions
دوره 39 شماره
صفحات -
تاریخ انتشار 2006