New, ionic side-products in oligonucleotide synthesis: formation and reactivity of fluorescent N-/purin-6-yl/pyridinium salts1
Open Access
- 1 January 1985
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 13 (8) , 2989-3003
- https://doi.org/10.1093/nar/13.8.2989
Abstract
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.Keywords
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