title: Synthesis and properties of oligodeoxynucleotides incorporating 5-carboxydeoxycytidine.
abstract: We synthesized oligodeoxynucleotide derivatives containing 5-carboxydeoxycytidine (1) as a new deoxynucleoside derivative having an anionic residue at the base part. The base pairing properties of the 5-carboxycytosine base were evaluated by use of ab initio calculations at the MP2/6-31G++(2d,p)//HF/6-31G(d) level. These calculations suggest that the Hoogsteen-type hydrogen bond in DNA triplex is less stable than that of the canonical C(+)-G pair and that the Watson-Crick base pair of this modified base with G is slightly more stable than the natural G-C base pair. These expectations were confirmed by T(m) experiments of duplexes and triplexes formed by hybridization of an oligodeoxynucleotide 14mer incorporating 5-carboxydeoxycytidine with ssDNA and dsDNA oligomers, respectively.
authors.affiliation: Department of Life Science, Tokyo Institute of Technology, Japan.
authors.forename: Masanori
authors.initials: M
authors.lastname: Sumino
authors.forename: Okamoto
authors.initials: O
authors.lastname: Itaru
authors.forename: Akihiro
authors.initials: A
authors.lastname: Ohkubo
authors.forename: Haruhiko
authors.initials: H
authors.lastname: Taguchi
authors.forename: Kohji
authors.initials: K
authors.lastname: Seio
authors.forename: Mitsuo
authors.initials: M
authors.lastname: Sekine
mesh_terms: D020029:Base Pairing; D004247:DNA / Q000737:chemistry; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: C528358:5-carboxydeoxycytidine; D009838:Oligodeoxyribonucleotides; C051802:triplex DNA; D003841:Deoxycytidine; D004247:DNA