Synthesis of oligo- and polynucleotides I. Synthesis of three pentadeoxyribonucleotides corresponding to the 5′-terminal secton of yeast valine tRNA

Badashkeeva, A. G.; Berlin, Yu. A.; Boldyreva, E. F.; Ivanovskaya, M. G.; Knorre, D.G.; Kolosov, M. N.; Korobko, V. G.; Prokof'ev, M. A.; Smirnov, V. D.; Shabarova, Z. A.; Shubina, T. N.

doi:10.1007/bf00565694

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“…The data obthided in the course of investigation oif the internuolootide bond for'ation revealed a number of byr-processes aoco_nyingn oligonuclootide synthesis* The mlaln complioations occur due-to the presene in nuclootide and nuclooside component of internucleotide phosphate groups with nucleophilicity exceedi that of hydroxy group to be phosphorylated. Therefore all reactive fo of mono-and dinucleotide react more readily with internucleotide phosphate than with hydroxy group (29,33,37).…”

Section: Nucleic Acids Researchmentioning

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: Nucleic Acids Researchmentioning

confidence: 99%