title: Synthesis of 5-(1-propynyl)-2'-deoxyuridine 5'-(alpha-P-borano)triphosphate and kinetic characterization as a substrate for mmlv reverse transcriptase.
abstract: In order to introduce pyrimidine C5-propynyl modification into boranophosphate oligodeoxyribonucleotides (BP- ODNs), 5-(1-propynyl)-2'-deoxyuridine 5'-(alpha-P-borano) triphosphate (d5PUTPalphaB) was synthesized. The two diastereomers were separated by reverse-phase HPLC. Kinetic studies showed that the Rp isomer was a slightly better substrate for MMLV reverse transcriptase than thymidine triphosphate or Rp-thymidine 5'-(alpha-P-borano)triphosphate. Using the Rp isomers of d5PUTPalphaB and the other three 5'-(alpha-P-borano) triphosphates, a DNA primer could be extended to the full length of the template.
authors.affiliation: Department of Chemistry, P.M. Gross Chemical Laboratory, Duke University, Durham, North Carolina, USA.
authors.forename: Joy Xin
authors.initials: JX
authors.lastname: Wang
authors.forename: Barbara Ramsay
authors.initials: BR
authors.lastname: Shaw
mesh_terms: D001895:Boron / Q000737:chemistry; D001896:Boron Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D004247:DNA / Q000737:chemistry; D017931:DNA Primers / Q000737:chemistry; D054303:HIV Reverse Transcriptase / Q000737:chemistry; D007700:Kinetics; D008956:Models, Chemical; D008979:Moloney murine leukemia virus / Q000235:genetics; D009711:Nucleotides / Q000737:chemistry; D009841:Oligonucleotides / Q000737:chemistry*; D011122:Polyphosphates / Q000737:chemistry; D020033:Protein Isoforms; D011743:Pyrimidines / Q000737:chemistry; D012194:RNA-Directed DNA Polymerase / Q000737:chemistry; D013936:Thymidine / Q000737:chemistry; D013942:Thymine Nucleotides / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives / Q000737:chemistry; D014544:Uridine Triphosphate / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: C506208:5-(1-propynyl)-2'-deoxyuridine 5'-(alpha-P-borano)triphosphate; D001896:Boron Compounds; D017931:DNA Primers; D009711:Nucleotides; D009841:Oligonucleotides; D011122:Polyphosphates; D020033:Protein Isoforms; D011743:Pyrimidines; D013942:Thymine Nucleotides; C432543:uridine-2',3'-cyclic boranophosphate; D004247:DNA; D054303:HIV Reverse Transcriptase; D012194:RNA-Directed DNA Polymerase; D001895:Boron; C005692:triphosphoric acid; C024157:thymidine 5'-triphosphate; D014544:Uridine Triphosphate; D013936:Thymidine; D014529:Uridine