Copper carbenes alkylate guanine chemoselectively through a substrate directed reaction
Geigle, Stefanie N.
Wyss, Laura A.
Gillingham, Dennis G.
- Journal Article
Rights / licenseCreative Commons Attribution-NonCommercial 3.0 Unported
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. Show more
Journal / seriesChemical Science
Pages / Article No.
PublisherRoyal Society of Chemistry
Organisational unit03853 - Sturla, Shana / Sturla, Shana
03853 - Sturla, Shana / Sturla, Shana
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