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Nucleic Acids Research, 1987, Vol. 15, No. 20 8333-8349
© 1987

Articles

Guanine modification daring chemical DNA synthesis

J.Scott Eadie* and D.Scott Davidson

Applied Biosystems, Inc., 850 Lincoln Centre Drive Foster City, CA 94404, USA

*To whom correspondence should be addressed

Received July 2, 1987. Revised September 25, 1987. Accepted September 25, 1987.

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.


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