A DNA duplex containing the primary acrolein adduct, 3-(2-deoxy-β-D-erythro-pentofuranosyl)-5,6,7,8-tetrahydro-8- hydroxypyrimido[1,2-a]purin-10(3H)-one (2), of deoxyguanosine in a 5′-CpG sequence context spontaneously but reversibly formed an interchain cross-link with the exocyclic amino group of deoxyguanosine in the opposing chain. The linkage was sufficiently stable that the cross-linked duplex could be isolated by HPLC and characterized by MALDI-TOF mass spectrometry. Enzymatic degradation gave bis-nucleoside 6, which was independently prepared by direct reaction of 2 with dGuo.
ASJC Scopus subject areas
- Drug Discovery
- Organic Chemistry
- Health, Toxicology and Mutagenesis