Reaction of a nucleoside 2,4-dinitrophenyl phosphate with fluoride; A convenient method for the preparation of the nucleoside phosphorfluoridate

Johnson, Paul W.; Tigerstrom, Richard von; Smith, Michael J.

doi:10.1093/nar/2.10.1745

Cited by 2 publications

(1 citation statement)

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“…These derivatives do not lead to colored substances and give only small amounts of side products. Some other approaches to the formation of internucleotide bonds were proposed;a method involving oxidationreduction condensation starting with triphenylphosphine and 2,2'-dipyridyldisulfide (3,4]; a method involving the activation of the hydroxy group of the nucleoside component with potassium butylate (5)(6)(7)(8)]; a method based on the use of oxyphosphoranes capable to react selectively at first with primary hydroxy group of one component and then with secondary hydroxy group of another component [(9-1l . The methods mentioned are very promising and in the future they will probably find wide applications.…”

Section: Introductionmentioning

confidence: 99%

The mechanism of the chemical synthesis of oligonucleotides and its synthetic consequences

Knorre

Зарытова

1976

Nucleic Acids Research

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The data obtained mainly by pulsed NMR spectroscopy on phosphorus nuclei on the mechanism of the internucleotide phosphodiester (PDE) group formation are summarised. With arylsulphonyl chloride as condensing reagent monomeric nucleotide derivative B (nucleoside metaphosphate or its pyridinium adduct) is the highly reactive intermediate. In the presence of PDE groups in nucleoside or nucleotide component the significantly less reactive derivatives with trisubstituted pyrophosphoryl residues are formed both with arylsulphonyl chloride and dicyclohexylcarbodiimide (DCC). The reactive B form of nucleotide component may be obtained using greater excess of arylsulphonyl chloride with simultaneous convertion of PDE groups to tetrasubstituted pyrophosphates amenable to side reactions. The convertion of PDE groups to easily hydrolysable dicyclohexylurea derivatives by reaction with DCC is proposed to reversible blocking of PDE groups of nucleoside component. The B type derivatives of mononucleotides or oligonucleotides with blocked PDE groups seems to be the best nucleotide components.

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Section: Introductionmentioning

confidence: 99%