title: Polymerase-catalyzed synthesis of DNA from phosphoramidate conjugates of deoxynucleotides and amino acids.
abstract: Some selected amino acids, in particular L-aspartic acid (L-Asp) and L-histidine (L-His), can function as leaving group during polymerase-catalyzed incorporation of deoxyadenosine monophosphate (dAMP) in DNA. Although L-Asp-dAMP and L-His-dAMP bind, most probably, in a different way in the active site of the enzyme, aspartic acid and histidine can be considered as mimics of the pyrophosphate moiety of deoxyadenosine triphosphate. L-Aspartic acid is more efficient than D-aspartic acid as leaving group. Such P-N conjugates of amino acids and deoxynucleotides provide a novel experimental ground for diversifying nucleic acid metabolism in the field of synthetic biology.
authors.affiliation: Rega Institute for Medical Research, Katholieke Universiteit Leuven, Department of Pharmaceutical Chemistry, Minderbroedersstraat 10, 3000 Leuven, Belgium.
authors.forename: O
authors.initials: O
authors.lastname: Adelfinskaya
authors.forename: M
authors.initials: M
authors.lastname: Terrazas
authors.forename: M
authors.initials: M
authors.lastname: Froeyen
authors.forename: P
authors.initials: P
authors.lastname: Marlière
authors.forename: K
authors.initials: K
authors.lastname: Nauwelaerts
authors.forename: P
authors.initials: P
authors.lastname: Herdewijn
mesh_terms: D000249:Adenosine Monophosphate / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D000577:Amides / Q000138:chemical synthesis / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry; D001224:Aspartic Acid / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D004247:DNA / Q000096:biosynthesis* / Q000737:chemistry; D017931:DNA Primers; D004259:DNA-Directed DNA Polymerase / Q000378:metabolism*; D003838:Deoxyadenine Nucleotides / Q000737:chemistry / Q000378:metabolism; D006678:HIV / Q000201:enzymology; D006639:Histidine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism; D008958:Models, Molecular; D010756:Phosphoric Acids / Q000138:chemical synthesis / Q000737:chemistry*; D012194:RNA-Directed DNA Polymerase / Q000737:chemistry / Q000378:metabolism; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D017931:DNA Primers; D003838:Deoxyadenine Nucleotides; D010756:Phosphoric Acids; C523302:aspartyl-deoxyadenosine monophosphate; C523303:histidyl-deoxyadenosine monophosphate; D001224:Aspartic Acid; D000249:Adenosine Monophosphate; D006639:Histidine; C012873:2'-deoxy-5'-adenosine monophosphate; D004247:DNA; C011067:phosphoramidic acid; D012194:RNA-Directed DNA Polymerase; D004259:DNA-Directed DNA Polymerase