Nucleoside and deoxynucleoside phosphorylation in formamide solutions. 1982

A M Schoffstall, and R J Barto, and D L Ramos

Nucleosides or deoxynucleosides were converted to a number of phosphorylated nucleotide and deoxynucleotide derivatives by ammonium of alkali dihydrogen phosphates in formamide. Conversions were smaller and slower at room temperature and greater and faster at elevated temperatures. Nucleotides afforded product mixtures to those obtained for nucleosides under the same conditions, indicating the occurrence of transphosphorylation processes. Products of the reaction at elevated temperatures were cyclic nucleotides, nucleoside monophosphates, nucleoside diphosphates and cyclic nucleotide phosphates. The relative amounts of products formed were quite temperature dependent. Cyclic nucleotides were found to be in greatest abundance for reactions run at 125 degree or above. Relative yields of 2',3' and 5' nucleotides and 3' and 5' deoxynucleotides from several experiments are reported. 5'Monophosphates were generally found to be present in larger quantities than 2' or 3' monophosphates. 2'-Deoxyadenosine showed a preference for phosphorylation at the 3' position. Conclusion reached from mechanistic studies are that the phosphorylations are a series of equilibrium reactions, with cyclic nucleotides being formed irreversibly.

UI MeSH Term Description Entries
D010766 Phosphorylation The introduction of a phosphoryl group into a compound through the formation of an ester bond between the compound and a phosphorus moiety. Phosphorylations
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
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
D003853 Deoxyribonucleosides A purine or pyrimidine base bonded to DEOXYRIBOSE.
D003854 Deoxyribonucleotides A purine or pyrimidine base bonded to a DEOXYRIBOSE containing a bond to a phosphate group. Deoxyribonucleotide
D005559 Formamides A group of amides with the general formula of R-CONH2.
D012263 Ribonucleosides Nucleosides in which the purine or pyrimidine base is combined with ribose. (Dorland, 28th ed)
D012265 Ribonucleotides Nucleotides in which the purine or pyrimidine base is combined with ribose. (Dorland, 28th ed) Ribonucleoside Phosphates,Ribonucleotide,Phosphates, Ribonucleoside
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

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