title: Unusual C7- versus Normal 5'-O-Dimethoxytritylation of 6-Arylpyrrolocytidine Analogs.
abstract: Fluorescent deoxynucleosides possessing the modified bases 6-(2-benzo[b]furyl)- and 6-(2-furyl)pyrrolocytosine (BFpC and FpC) have been synthesized along with the quencher nucleosides possessing 6-{4-[(4-dimethylamino)azo]phenyl}pyrrolocytosine (DABCYLpC) and 6-(p-nitrophenyl)pyrrolocytosine (p-NO2-PhpC) nucleobase analogs. Standard treatment of BFpC, FpC, DABCYLpC, and p-NO2-PhpC with dimethoxytrityl chloride (DMT-Cl) led to the unusual substitution on the C7 of the pyrrolocytosine skeleton. The desired 5'-O-DMT-protected nucleoside analogs were synthesized from suitably protected 5'-O-DMT cytidines. Subsequent phosphitylation smoothly afforded BFpC-, FpC-, DABCYLpC-, and p-NO2-PhpC-derived monomers suitable for standard oligonucleotide synthesis.
authors.affiliation: Department of Chemistry and ‡The Centre for Advanced Materials and Biomaterials Research, The University of Western Ontario , London, Ontario N6A 5B7, Canada.
authors.forename: Mojmír
authors.initials: M
authors.lastname: Suchý
authors.affiliation: Department of Chemistry and ‡The Centre for Advanced Materials and Biomaterials Research, The University of Western Ontario , London, Ontario N6A 5B7, Canada.
authors.forename: Christie
authors.initials: C
authors.lastname: Ettles
authors.affiliation: Department of Chemistry and ‡The Centre for Advanced Materials and Biomaterials Research, The University of Western Ontario , London, Ontario N6A 5B7, Canada.
authors.forename: James A
authors.initials: JA
authors.lastname: Wisner
authors.affiliation: Department of Chemistry and ‡The Centre for Advanced Materials and Biomaterials Research, The University of Western Ontario , London, Ontario N6A 5B7, Canada.
authors.forename: Augusto
authors.initials: A
authors.lastname: Matarazzo
authors.affiliation: Department of Chemistry and ‡The Centre for Advanced Materials and Biomaterials Research, The University of Western Ontario , London, Ontario N6A 5B7, Canada.
authors.forename: Robert H E
authors.initials: RH
authors.lastname: Hudson