Open AccessGuanine modification daring chemical DNA synthesis
Author(s) -
J. Eadie,
D.Scott Davidson
Publication year - 1987
Publication title -
nucleic acids research
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 9.008
H-Index - 537
eISSN - 1362-4954
pISSN - 0305-1048
DOI - 10.1093/nar/15.20.8333
Subject(s) - guanine , phosphoramidite , chemical modification , biology , deoxyribonucleoside , ammonium hydroxide , nucleoside , dna , fluorescence , combinatorial chemistry , chemical synthesis , biochemistry , nucleic acid , oligonucleotide , nucleotide , organic chemistry , chemistry , gene , physics , quantum mechanics , in vitro
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.