Ferrocene-modified pyrimidine nucleosides: synthesis, structure and electrochemistry.
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.
Song
Haifeng
H
Department of Chemistry, University of Saskatchewan, Saskatoon, SK, CanadaS7N 5C9.
Li
Xiaohong
X
Long
Yitao
Y
Schatte
Gabriele
G
Kraatz
Heinz-Bernhard
HB
D018360:Crystallography, X-Ray; D004247:DNA / Q000737:chemistry; D003841:Deoxycytidine / Q000737:chemistry; D003857:Deoxyuridine / Q000737:chemistry; D004563:Electrochemistry; D004583:Electrons; D005296:Ferrous Compounds / Q000737:chemistry*; D000075163:Metallocenes; D015394:Molecular Structure; D009841:Oligonucleotides / Q000737:chemistry; D010084:Oxidation-Reduction; D011741:Pyrimidine Nucleosides / Q000737:chemistry*
D005296:Ferrous Compounds; D000075163:Metallocenes; D009841:Oligonucleotides; D011741:Pyrimidine Nucleosides; D003841:Deoxycytidine; D004247:DNA; C004998:ferrocene; D003857:Deoxyuridine