title: Synthesis of nucleoside 5'-tetraphosphates containing terminal fluorescent labels via activated cyclic trimetaphosphate.
abstract: 2'-Deoxynucleotide 5'-tetraphosphates in which a fluorescent label is attached to the terminal phosphate are used as key reagents in high-throughput DNA sequencing techniques and in single nucleotide polymorphism typing assays. We demonstrate that this class of compounds can be prepared by reacting fluorophores such as 7-hydroxy-4-methylcoumarin, methylfluorescein, fluorescein and resorufin with an activated form of cyclic trimetaphosphate to give intermediate 11. Reaction of 11 with 2'-deoxynucleoside 5'-monophosphates or a nucleoside 5'-monophosphate gave the target compounds in good yield.
authors.affiliation: Department of Chemistry, University of Waterloo , 200 University Avenue West, Waterloo, Ontario, Canada.
authors.forename: Samy
authors.initials: S
authors.lastname: Mohamady
authors.forename: Scott D
authors.initials: SD
authors.lastname: Taylor
mesh_terms: D004247:DNA / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000737:chemistry*; D007202:Indicators and Reagents / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D009711:Nucleotides / Q000138:chemical synthesis* / Q000737:chemistry*; D011122:Polyphosphates / Q000737:chemistry*; D014468:Umbelliferones / Q000737:chemistry*
chemical_list: D005456:Fluorescent Dyes; D007202:Indicators and Reagents; D009705:Nucleosides; D009711:Nucleotides; D011122:Polyphosphates; D014468:Umbelliferones; D004247:DNA; C009293:trimetaphosphoric acid