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Nucleic Acids Research, 1985, Vol. 13, No. 8 2989-3003
© 1985

Articles

New, ionic side-products in oligonucleotide synthesis: formation and reactivity of fluorescent N-/purin-6-yl/pyridinium salts1

Ryszard W. Adamiak, Ewa Biata and Bohdan Skalski

Institute of Bioorganic Chemistry, Polish Academy of Sciences 61-704 Poznan, Noskowskiego 12/14, Poland Faculty of Chemistry, Adam Mickiewicz University 60-780 Poznan Grunwaldzka 6, Poland

Received January 29, 1985. Revised March 25, 1985. Accepted March 19, 1985.

Fluorescent N-/purin-6-yl/pyridinium salts are formed in pyridine assisted phosphorylations and arenesulphonations of the hypoxanthine lactam system under various conditions including those used in oligonucleotide synthesis. The N1-methyl-N3-/pur in-6-yl/imidazolium salt is generated in phosphorylation with TPSC1/1-methylimidazole as a coupling system. Both salts are representatives of a new family of ionic side-products in oligonucleotide synthes is involving hypoxanthine residues. Their isolation procedure has been developed. High reactivity of N-/purin-6-yl/pyridinium salts towards some reagents used in oligonucleotide chemistry, e.g. pyridinium mediated conversion of hypoxanthine into 6-aminopurine, can result in point mutations in synthesized oligomer.


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