BIOMAT Database Logo BIOMAT Database Logo

The synthesis, conformation and hydrolytic stability of an N,S-bridging thiophosphoramidate analogue of thymidylyl-3',5'-thymidine. 2016

Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
Department of Chemistry, Durham University, South Road, Durham, DH1 3LE, UK. d.r.w.hodgson@durham.ac.uk.

A 3'-N,5'-S-bridging thiophosphoramidate analogue of thymidylyl-3',5'-thymidine was synthesised under aqueous conditions. (1)H NMR conformational measurements show that the 3'-N-substituted deoxyribose ring is biased towards the 'north', RNA-like conformation. Rate constants for hydrolysis of the analogue were measured at 90 °C in the pH range 1.3-10.9. The pH-log kobs profile displays a pH-independent region between approximately pH 7 and 10 (t1/2 ∼13 days). Under acidic conditions, kobs displays a first order dependence on [H3O(+)].

UI MeSH Term Description Entries
D007700 Kinetics The rate dynamics in chemical or physical systems.
D008968 Molecular Conformation The characteristic three-dimensional shape of a molecule. Molecular Configuration,3D Molecular Structure,Configuration, Molecular,Molecular Structure, Three Dimensional,Three Dimensional Molecular Structure,3D Molecular Structures,Configurations, Molecular,Conformation, Molecular,Conformations, Molecular,Molecular Configurations,Molecular Conformations,Molecular Structure, 3D,Molecular Structures, 3D,Structure, 3D Molecular,Structures, 3D Molecular
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D009943 Organophosphorus Compounds Organic compounds that contain phosphorus as an integral part of the molecule. Included under this heading is broad array of synthetic compounds that are used as PESTICIDES and DRUGS. Organophosphorus Compound,Organopyrophosphorus Compound,Organopyrophosphorus Compounds,Compound, Organophosphorus,Compound, Organopyrophosphorus,Compounds, Organophosphorus,Compounds, Organopyrophosphorus
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D003855 Deoxyribose 2-Deoxyribose,2 Deoxyribose
D006863 Hydrogen-Ion Concentration The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D015226 Dinucleoside Phosphates A group of compounds which consist of a nucleotide molecule to which an additional nucleoside is attached through the phosphate molecule(s). The nucleotide can contain any number of phosphates. Bis(5'-Nucleosidyl)Oligophosphates,Bis(5'-Nucleosidyl)Phosphates,Deoxydinucleoside Phosphates,Dinucleoside Diphosphates,Dinucleoside Monophosphates,Dinucleoside Oligophosphates,Dinucleoside Tetraphosphates,Dinucleoside Triphosphates,Bis(5'-Nucleosidyl)Tetraphosphate,Dinucleoside Polyphosphates,Diphosphates, Dinucleoside,Monophosphates, Dinucleoside,Oligophosphates, Dinucleoside,Phosphates, Deoxydinucleoside,Phosphates, Dinucleoside,Polyphosphates, Dinucleoside,Tetraphosphates, Dinucleoside,Triphosphates, Dinucleoside

Related Publications

Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
Hydrolytic reactions of 3'-N-phosphoramidate and 3'-N-thiophosphoramidate analogs of thymidylyl-3',5'-thymidine.
February 2004, Organic & biomolecular chemistry,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
Crystal structure and photochemical behavior in solution of the 3'-N-sulfamate analogue of thymidylyl(3'-5')thymidine.
January 2007, The Journal of organic chemistry,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
THE ULTRAVIOLET PHOTOCHEMISTRY OF THYMIDYLYL-(3'-5')-THYMIDINE.
August 1964, Journal of molecular biology,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
The chemical stability of S-(2-acylthioethyl) and S-acyloxymethyl protected thymidylyl-3',5'-thymidine phosphoromonothiolates and their deacylation products in aqueous solution.
January 2001, Nucleosides, nucleotides & nucleic acids,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
A comparative conformational study of thymidylyl(3'----5')-thymidine, thymidylyl(3'----5')-5'-thio-5'- deoxythymidine and thymidinylacetamido-[3'(O)----5'(C)]-5'-deoxythymidine.
January 1990, Journal of biochemical and biophysical methods,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
Probing mechanism of metal catalyzed hydrolysis of Thymidylyl (3'-O, 5'-S) thymidine phosphodiester derivatives.
March 2013, Journal of molecular modeling,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
Sugar conformational effects on the photochemistry of thymidylyl(3'-5')thymidine.
August 2003, The Journal of organic chemistry,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
[The benzyl ester of desoxydinucleosidphosphate and 5'-0- (beta, beta) trichlorethylphosphorylthymidylyl-(3'-5')-thymidylyl-(3'-5') thymidine+)].
August 1967, Tetrahedron letters,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
Solution-state structure of the Dewar pyrimidinone photoproduct of thymidylyl-(3'----5')-thymidine.
September 1988, Biochemistry,
Louis P Conway, and Satu Mikkola, and AnnMarie C O'Donoghue, and David R W Hodgson
Nuclear magnetic resonance studies of cis-syn, trans-syn, and 6-4 photodimers of thymidylyl(3'-5')thymidine monophosphate and cis-syn photodimers of thymidylyl(3'-5')thymidine cyanoethyl phosphotriester.
July 1988, Biochemistry,
Copied contents to your clipboard!