title: Synthesis and properties of nucleic acid analogues consisting of a benzene-phosphate backbone.
abstract: [Chemical reaction: See text] The synthesis and properties of a nucleic acid analogue consisting of a benzene-phosphate backbone are described. The building blocks of the nucleic acid analogue are composed of bis(hydroxymethyl)benzene residues connected to nucleobases via the biaryl-like axis. Stabilities of the duplexes were studied by thermal denaturation. It was found that the thermal stabilities of the duplexes composed of the benzene-phosphate backbone are highly dependent on their sequences. The duplexes with the benzene-phosphate backbone comprised of the mixed sequences were thermally less stable than the natural DNA duplexes, whereas that composed of the homopyrimidine and homopurine sequences was thermally and thermodynamically more stable than the corresponding natural DNA duplex. It was suggested that the analogues more efficiently stabilize the duplexes in a B-form duplex rather than in an A-form duplex. Thus, the duplexes consisting of the benzene-phosphate backbone, especially composed of the homopyrimidine and homopurine sequences, may offer a novel structural motif useful for developing novel materials applicable in the fields of bio- and nanotechnologies.
authors.affiliation: Department of Biomolecular Science, Faculty of Engineering, Gifu University, Yanagido, Gifu 501-1193, Japan.
authors.forename: Yoshihito
authors.initials: Y
authors.lastname: Ueno
authors.forename: Takumi
authors.initials: T
authors.lastname: Kato
authors.forename: Kumiko
authors.initials: K
authors.lastname: Sato
authors.forename: Yasutomo
authors.initials: Y
authors.lastname: Ito
authors.forename: Mahito
authors.initials: M
authors.lastname: Yoshida
authors.forename: Takumi
authors.initials: T
authors.lastname: Inoue
authors.forename: Aya
authors.initials: A
authors.lastname: Shibata
authors.forename: Masahiro
authors.initials: M
authors.lastname: Ebihara
authors.forename: Yukio
authors.initials: Y
authors.lastname: Kitade
mesh_terms: D001483:Base Sequence; D001555:Benzene Derivatives; D002942:Circular Dichroism; D004355:Drug Stability; D007202:Indicators and Reagents; D008958:Models, Molecular; D008970:Molecular Weight; D009690:Nucleic Acid Conformation; D009691:Nucleic Acid Denaturation; D009696:Nucleic Acids / Q000138:chemical synthesis* / Q000737:chemistry*; D009838:Oligodeoxyribonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D009843:Oligoribonucleotides / Q000138:chemical synthesis / Q000737:chemistry; D010710:Phosphates; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization; D013816:Thermodynamics
chemical_list: D001555:Benzene Derivatives; D007202:Indicators and Reagents; D009696:Nucleic Acids; D009838:Oligodeoxyribonucleotides; D009843:Oligoribonucleotides; D010710:Phosphates