Guanine modification daring chemical DNA synthesis
Open Access
- 1 January 1987
- journal article
- Published by Oxford University Press (OUP) in Nucleic Acids Research
- Vol. 15 (20) , 8333-8349
- https://doi.org/10.1093/nar/15.20.8333
Abstract
Base modification during solid-phase phosphoramidite synthesis of oligodeoxynucleotides has been investigated. We have discovered chemical modification that converts dG and dG-containing oligomers to a fluorescent form. This modification has been linked to N, N-dimethylaminopyridine (DMAP), an acylation catalyst, which can displace phosphate triester adducts at the 6-position of guanine. Further, we have found that this fluorescent intermediate can be converted in ammonium hydroxide solution to 2, 6 diaminopurine deoxyribonucleoside (2, 6 DAP), a potentially mutagenic nucleoside analog. We have shown that N-methylimidazole (NMI) in place of DMAP eliminates the fluorescent species and reduces 2, 6 DAP contamination.Keywords
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