Synthesis of Nucleoside Tetraphosphates and Dinucleoside Pentaphosphates via Activation of Cyclic Trimetaphosphate

Abstract

A procedure for the synthesis of dinucleoside 5'-pentaphosphates (Np5N) and nucleoside 5'-tetraphosphates (Np4) is described. The procedure relies on the activation of cyclic trimetaphosphate followed by a reaction with a nucleoside 5'-monophosphate (NMP) to give intermediates of type 3. Reaction of 3 with water or an NMP gives the desired products in yields ranging from 77 to 86%.

References

Page 1

	Year	Citations
Intrinsic motions along an enzymatic reaction trajectory Katherine A. Henzler‐Wildman, Vu Thai, Ming Lei, Nature Intrinsic MotionsBiochemistryEnzyme CatalysisMacromolecular MachineStructure-function Enzyme Kinetics	2007	899
P1,P5-Di(adenosine-5′)pentaphosphate, a Potent Multisubstrate Inhibitor of Adenylate Kinase Gustav E. Lienhard, Isaac I. Secemski Journal of Biological Chemistry Muscle FunctionCellular PhysiologyAdenylate KinaseMolecular PharmacologyMuscle Physiology	1973	521
Synthetic Inhibitors of Adenylate Kinases in the Assays for ATPases and Phosphokinases Peter Feldhaus, Thomas Fröhlich, Roger S. Goody, European Journal of Biochemistry Muscle FunctionEscherichia ColiAdenosine TetraphosphateSynthetic InhibitorsChemical Biology	1975	182
Synthesis and P2Y receptor activity of a series of uridine dinucleoside 5′-polyphosphates William Pendergast, Benjamin R. Yerxa, James G. Douglass, Bioorganic & Medicinal Chemistry Letters Molecular PharmacologyP2y Receptor ActivityBioorganic ChemistryBiochemistryG Protein-coupled Receptor	2001	120
Fluorogenic DNA sequencing in PDMS microreactors Peter A. Sims, William J. Greenleaf, Haifeng Duan, Nature Methods Dna SequencingEngineeringMicroscopyMicrofabricationMedicine	2011	80
Stereochemical courses of nucleotidyltransferase and phosphotransferase action. Uridine diphosphate glucose pyrophosphorylase, galactose-1-phosphate uridylyltransferase, adenylate kinase, and nucleoside diphosphate kinase Kwan‐Fu Rex Sheu, John P. Richard, Perry A. Frey Biochemistry Chemical BiologyBiosynthesisSignal TransductionCellular EnzymologyBiochemistry	1979	72
Sulfonyl Imidazolium Salts as Reagents for the Rapid and Efficient Synthesis of Nucleoside Polyphosphates and Their Conjugates Samy Mohamady, Ahmed Desoky, Scott D. Taylor Organic Letters Combinatorial ChemistryBiosynthesisBioorganic ChemistrySulfonyl Imidazolium SaltsBiochemistry	2011	69
Synthesis and potency of novel uracil nucleotides and derivatives as P2Y2 and P2Y6 receptor agonists Hyojin Ko, Rhonda L. Carter, Liesbet Cosyn, Bioorganic & Medicinal Chemistry Molecular PharmacologyMedicinal ChemistryPharmaceutical ScienceBiochemistryNovel Uracil Nucleotides	2008	67
Influence of Electric Charge Variation at Residues 209 and 159 on the Interaction of eIF4E with the mRNA 5‘ Terminus Joanna Zuberek, Jacek Jemielity, Agnieszka Jabłonowska, Biochemistry	2004	66
Phosphotriester approach to the synthesis of oligonucleotides: a reappraisal Colin B. Reese, Peizhuo Zhang Journal of the Chemical Society Perkin Transactions 1 BiosynthesisBioorganic ChemistryEngineeringBiochemistryNesulfonyl Chlorides	1993	64

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