Synthesis and stability of oligodeoxynucleotides containing C8-labeled 2'-deoxyadenosine: novel redox nucleobase probes for DNA-mediated charge-transfer studies.
[reaction: see text] An efficient and convenient synthetic strategy to redox-labeled C8-derivatives of 2'-deoxyadenosine is described. The Pd(0) cross-coupling chemistry is amenable to both oxidative and reductive redox probes. The corresponding phosphoramidites of phenothiazine and anthraquinone nucleosides are amenable to automated DNA synthesis. The resulting labeled oligodeoxynucleotide strands form stable B-form duplexes with melting temperatures and CD spectra similar to those of the unlabeled analogues.
Tierney
M T
MT
Department of Chemistry, Paul M. Gross Chemical Laboratory, Duke University, Durham, North Carolina 27708, USA.
Grinstaff
M W
MW
D001483:Base Sequence; D004247:DNA / Q000737:chemistry*; D015342:DNA Probes; D003839:Deoxyadenosines; D004355:Drug Stability; D007202:Indicators and Reagents; D009690:Nucleic Acid Conformation; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction
D015342:DNA Probes; D003839:Deoxyadenosines; D007202:Indicators and Reagents; D009838:Oligodeoxyribonucleotides; D004247:DNA