Copper carbenes alkylate guanine chemoselectively through a substrate directed reaction.
Chem Sci
; 8(1): 499-506, 2017 Jan 01.
Article
em En
| MEDLINE
| ID: mdl-28451197
ABSTRACT
Cu(i) carbenes derived from α-diazocarbonyl compounds lead to selective alkylation of the O6 position in guanine (O6-G) in mono- and oligonucleotides. Only purine-type lactam oxygens are targeted - other types of amides or lactams are poorly reactive under conditions that give smooth alkylation of guanine. Mechanistic studies point to N7G as a directing group that controls selectivity. Given the importance of O6-G adducts in biology and biotechnology we expect that Cu(i)-catalyzed O6-G alkylation will be a broadly used synthetic tool. While the propensity for transition metals to increase redox damage is well-appreciated, our results suggest that transition metals might also increase the vulnerability of nucleic acids to alkylation damage.
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MEDLINE
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Ano de publicação:
2017
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Article