title: Synthesis and oligonucleotide incorporation of fluorescent cytosine analogue tC: a promising nucleic acid probe.
abstract: The tricyclic cytosine, tC, is a fluorescent base analogue with excellent properties for investigating intrinsic characteristics of nucleic acid as well as interactions between nucleic acids and other molecules. Its unique fluorescence properties and insignificant influence on overall structure and dynamics of nucleic acid after incorporation makes tC particularly interesting in fluorescence resonance energy transfer and anisotropy measurements. We here describe a straightforward synthesis of the standard monomer form of tC for DNA solid-phase synthesis, the tC phosphoramidite, and its subsequent incorporation into oligonucleotides. The total synthesis of the tC phosphoramidite takes approximately 8 days and its incorporation and the subsequent oligonucleotide purification an additional day.
authors.affiliation: Department of Chemical and Biological Engineering/Physical Chemistry, Chalmers University of Technology, SE-41296 Gothenburg, Sweden.
authors.forename: Peter
authors.initials: P
authors.lastname: Sandin
authors.forename: Per
authors.initials: P
authors.lastname: Lincoln
authors.forename: Tom
authors.initials: T
authors.lastname: Brown
authors.forename: L Marcus
authors.initials: LM
authors.lastname: Wilhelmsson
mesh_terms: D003596:Cytosine / Q000737:chemistry; D005456:Fluorescent Dyes / Q000737:chemistry; D015394:Molecular Structure; D015341:Nucleic Acid Probes / Q000138:chemical synthesis* / Q000737:chemistry*; D009841:Oligonucleotides / Q000737:chemistry; D009943:Organophosphorus Compounds / Q000737:chemistry
chemical_list: D005456:Fluorescent Dyes; D015341:Nucleic Acid Probes; D009841:Oligonucleotides; D009943:Organophosphorus Compounds; C434331:phosphoramidite; D003596:Cytosine