943446-55-7Relevant academic research and scientific papers
Gemcitabine, Pyrrologemcitabine, and 2′-Fluoro-2′-Deoxycytidines: Synthesis, Physical Properties, and Impact of Sugar Fluorination on Silver Ion Mediated Base Pairing
Guo, Xiurong,Leonard, Peter,Ingale, Sachin A.,Seela, Frank
, p. 17740 - 17754 (2017)
The stability of silver-mediated “dC-dC” base pairs relies not only on the structure of the nucleobase, but is also sensitive to structural modification of the sugar moiety. 2′-Fluorinated 2′-deoxycytidines with fluorine atoms in the arabino (up) and ribo (down) configuration as well as with geminal fluorine substitution (anticancer drug gemcitabine) and the novel fluorescent phenylpyrrolo-gemcitabine (phPyrGem) have been synthesized. All the nucleosides display the recognition face of naturally occurring 2′-deoxycytidine. The nucleosides were converted into phosphoramidites and incorporated into 12-mer oligonucleotides by solid-phase synthesis. The addition of silver ions to DNA duplexes with a fluorine-modified “dC-dC” pair near the central position led to significant duplex stabilization. The increase in stability was higher for duplexes with fluorinated sugar residues than for those with an unchanged 2′-deoxyribose moiety. Similar observations were made for “dC-dT” pairs and to a minor extent for “dC-dA” pairs. The increase in silver ion mediated base-pair stability was reversed by annulation of a pyrrole ring to the cytosine moiety, as shown for 2′-fluorinated phPyrGem in comparison with phenylpyrrolo-dC (phPyrdC). This phenomenon results from stereoelectronic effects induced by fluoro substitution, which are transmitted from the sugar moiety to the silver ion mediated base pairs. The extent of the effect depends on the number of fluorine substituents, their configuration, and the structure of the nucleobase.
Unusual C7- versus Normal 5′-O-Dimethoxytritylation of 6-Arylpyrrolocytidine Analogs
Suchy, Mojmír,Ettles, Christie,Wisner, James A.,Matarazzo, Augusto,Hudson, Robert H. E.
, p. 8415 - 8425 (2016/09/28)
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.
Selective fluorometric detection of guanosine-containing sequences by 6-phenylpyrrolocytidine in DNA
Hudson, Robert H. E.,Ghorbani-Choghamarani, Arash
, p. 870 - 873 (2008/02/03)
The intrinsically fluorescent nucleoside 2′-deoxy-6- phenylpyrrolocytidine, when incorporated into an oligonucleotide, is selectively quenched by hybridization with match DNA vs. mismatched sequences. Georg Thieme Verlag Stuttgart.
