ChemInform Abstract: SYNTHESIS OF 5′‐TERMINAL PHOSPHATE DERIVATIVES OF DINUCLEOTIDES USING ARYLSULFONYL CHLORIDES

Badashkeeva, A. G.; Зарытова, В. Ф.; Urmanov, I. Kh.; Shubina, T. N.

doi:10.1002/chin.197626338

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“…The last compound may be separated from polymer to be used for oligonucleotide synthesis. Dinucleotide derivative of the C type separated from polymer reacts readily with amines and the reaction may be used for indroducing of the amide blocking group on the 5'-end of dinucleotide [49],…”

Section: Synthetio Conseqluencesmentioning

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: Synthetio Conseqluencesmentioning

confidence: 99%