title: Synthesis of acetylene linked double-nucleobase nucleos(t)ide building blocks and polymerase construction of DNA containing cytosines in the major groove.
abstract: (Cytosin-5-yl)ethynyl derivatives of pyrimidine and 7-deazaadenine 2-deoxyribonucleosides and nucleoside triphosphates (dNTPs) were prepared in one step by the aqueous Sonogashira coupling of unprotected halogenated nucleos(t)ides with 5-ethynylcytosine. The modified dNTPs were good substrates for DNA polymerases suitable for primer extension or PCR construction of DNA bearing acetylene-linked cytosine(s) in the major groove mimicking the flipped-out nucleotide.
authors.affiliation: Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Gilead Sciences & IOCB Research Center, Flemingovo nam.2, CZ-16610 Prague 6, Czech Republic.
authors.forename: Pavel
authors.initials: P
authors.lastname: Kielkowski
authors.forename: Radek
authors.initials: R
authors.lastname: Pohl
authors.forename: Michal
authors.initials: M
authors.lastname: Hocek
mesh_terms: D000114:Acetylene / Q000737:chemistry*; D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry; D001483:Base Sequence; D003596:Cytosine / Q000737:chemistry*; D004247:DNA / Q000737:chemistry* / Q000235:genetics / Q000378:metabolism; D004259:DNA-Directed DNA Polymerase / Q000737:chemistry / Q000378:metabolism*; D008958:Models, Molecular; D009690:Nucleic Acid Conformation; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry; D014498:Uracil / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D009705:Nucleosides; D009711:Nucleotides; C043837:7-deazaadenine; D014498:Uracil; D003596:Cytosine; D004247:DNA; D004259:DNA-Directed DNA Polymerase; D000225:Adenine; D000114:Acetylene