Synthesis of 5-(1-propynyl)-2'-deoxyuridine 5'-(alpha-P-borano)triphosphate and kinetic characterization as a substrate for mmlv reverse transcriptase.
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.
Wang
Joy Xin
JX
Department of Chemistry, P.M. Gross Chemical Laboratory, Duke University, Durham, North Carolina, USA.
Shaw
Barbara Ramsay
BR
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
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