Synthesis and characterization of fluorenone-, anthraquinone-, and phenothiazine-labeled oligodeoxynucleotides: 5'-probes for DNA redox chemistry.
A facile and automated procedure for the synthesis of oligodeoxynucleotides possessing derivatives of 9-fluoreneone, 9,10-anthraquinone, and phenothiazine is described. The phosphoramidite approach is used to attach these redox and spectroscopic probes to the 5'-terminus of oligodeoxynucleotides in high yield (>95%). Thermal denaturation studies of labeled oligodeoxynucleotides show a slight enhancement in duplex stability relative to the unlabeled control, and circular dichroism spectra confirm B-form helical DNA structure in solution.
Tierney
M T
MT
Department of Chemistry, Duke University, Durham, North Carolina 27708, USA.
Grinstaff
M W
MW
D000880:Anthraquinones / Q000737:chemistry*; D001483:Base Sequence; D004247:DNA / Q000138:chemical synthesis* / Q000737:chemistry; D015342:DNA Probes; D005449:Fluorenes / Q000737:chemistry*; D010084:Oxidation-Reduction; D010640:Phenothiazines / Q000737:chemistry*
D000880:Anthraquinones; D015342:DNA Probes; D005449:Fluorenes; D010640:Phenothiazines; D004247:DNA