title: Sulfonate derived phosphoramidates as active intermediates in the enzymatic primer-extension of DNA.
abstract: Novel unnatural 5'-phosphoramidate nucleosides, capable of being processed as substrates by DNA polymerases for multiple nucleotide incorporations, have been designed. The mimics feature metabolites such as taurine and a broad range of aliphatic sulfonates coupled through a P-N bond to the 5'-phosphate position of deoxynucleotides, to allow binding interactions in the enzyme active site. The utility of all of the analogues as pyrophosphate mimics was demonstrated for the chain elongation of DNA, using both thermophilic and mesophilic microbial polymerases.
authors.affiliation: Medicinal Chemistry, Rega Institute for Medical Research, KU Leuven, Minderbroedersstraat 10, 3000 Leuven, Belgium. Piet.Herdewijn@rega.kuleuven.be.
authors.forename: S
authors.initials: S
authors.lastname: De
authors.forename: E
authors.initials: E
authors.lastname: Groaz
authors.forename: L
authors.initials: L
authors.lastname: Margamuljana
authors.forename: M
authors.initials: M
authors.lastname: Abramov
authors.forename: P
authors.initials: P
authors.lastname: Marlière
authors.forename: P
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D000577:Amides / Q000737:chemistry*; D020134:Catalytic Domain; D004247:DNA / Q000737:chemistry* / Q000378:metabolism*; D017931:DNA Primers / Q000378:metabolism*; D004259:DNA-Directed DNA Polymerase / Q000737:chemistry / Q000378:metabolism*; D007700:Kinetics; D009705:Nucleosides / Q000737:chemistry; D010756:Phosphoric Acids / Q000737:chemistry*; D013451:Sulfonic Acids / Q000737:chemistry*
chemical_list: D000577:Amides; D017931:DNA Primers; D009705:Nucleosides; D010756:Phosphoric Acids; D013451:Sulfonic Acids; D004247:DNA; C011067:phosphoramidic acid; D004259:DNA-Directed DNA Polymerase