title: Synthesis and hybridization properties of oligonucleotides having 4-N-(pyrrol-2-ylcarbonyl)deoxycytidine.
abstract: A new 4-N-acylated deoxycytidine derivative, 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine, was synthesized and found to be stable under rather basic conditions. Oligodeoxynucleotides (ODNs) incorporating this modified deoxynucleoside at various positions were successfully synthesized by using a pivaloyloxymethyl (POM) group for protection of the pyrrole residue. The POM group was removed by treatment with 1.5 M NaOMe/MeOH. ODNs containing modified deoxycytidines exhibited hybridization properties superior to those of the unmodified ODNs. We found the acylation of the cytosine base with an aromatic acyl-type substituent led to significant increase of the thermo stability of DNA duplexes. This is the first noteworthy observation in this kind of modification. The synthesis and hybridization properties of 4-N-(1H-pyrrol-2-ylcarbonyl)deoxycytidine derivatives will be also reported.
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, Yokohama 226-8501, Japan.
authors.forename: Ken
authors.initials: K
authors.lastname: Yamada
authors.forename: Hirosuke
authors.initials: H
authors.lastname: Tsunoda
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: D003841:Deoxycytidine / Q000737:chemistry*; D009693:Nucleic Acid Hybridization; D009841:Oligonucleotides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D009841:Oligonucleotides; D003841:Deoxycytidine