title: Synthesis of a fluorescent 2'3'-dideoxycytosine analog, tCdd.
abstract: The pathway leading to the preparation of a novel tricyclic 2'3'-dideoxycytosine analog, tCdd (1) is reported. A protected 2'3'-dideoxyribose prepared from l-glutamic acid was coupled to a silylated fluorescent base to yield a mixture of the alpha- and beta-anomers of the 2'3'-dideoxyribonucleoside of 1,3-diaza-2-oxophenothiazine, tCdd (1). The fluorescent base analog retains a high fluorescence emission over a large pH range and should be useful in a variety of probe applications.
authors.affiliation: Department of Chemistry and Biochemistry, University of San Diego, San Diego, CA 92110, USA.
authors.forename: William
authors.initials: W
authors.lastname: Porterfield
authors.forename: Deborah C
authors.initials: DC
authors.lastname: Tahmassebi
mesh_terms: D003596:Cytosine / Q000031:analogs & derivatives*; D003845:Deoxycytosine Nucleotides / Q000138:chemical synthesis*; D003855:Deoxyribose / Q000031:analogs & derivatives; D005453:Fluorescence; D005456:Fluorescent Dyes / Q000737:chemistry*; D018698:Glutamic Acid; D006863:Hydrogen-Ion Concentration; D015341:Nucleic Acid Probes / Q000138:chemical synthesis*
chemical_list: D003845:Deoxycytosine Nucleotides; D005456:Fluorescent Dyes; D015341:Nucleic Acid Probes; D018698:Glutamic Acid; D003855:Deoxyribose; D003596:Cytosine