544684-45-9Relevant academic research and scientific papers
Site-specific synthesis and reactivity of oligonucleotides containing stereochemically defined 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-Hydroxynonenal
Wang, Hao,Kozekov, Ivan D.,Harris, Thomas M.,Rizzo, Carmelo J.
, p. 5687 - 5700 (2007/10/03)
trans-4-Hydroxynonenal (HNE) is a major peroxidation product of ω-6 polyunsaturated fatty acids. The reaction of HNE with DNA gives four diastereomeric 1,N2-γ-hydroxypropano adducts of deoxyguanosine; background levels of these adducts have been detected in animal tissue. Stereospecific syntheses of these four adducts at the nucleoside level have been accomplished. In addition, a versatile strategy for their site-specific incorporation into oligonucleotides has been developed. These adducts are destabilizing as measured by melting temperature when compared to an unadducted strand. The thermal destablization of the adducted 12-mers ranged from 5 to 16 °C and is dependent on the absolute stereochemistry of the adduct. The HNE adducts were also examined for their ability to form interstrand DNA-DNA cross-links when incorporated into a CpG sequence. We find that only one of the HNE stereoisomers formed interstrand DNA-DNA cross-links.
Stereocontrolled syntheses of all four stereoisomeric 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal
Wang, Hao,Rizzo, Carmelo J.
, p. 3603 - 3605 (2007/10/03)
(formula presented) trans-4-Hydroxynonenal (4-HNE) is a unique product from the peroxidation of Α-6 polyunsaturated fatty acids. The major reaction of racemic 4-HNE with DNA is with deoxyguanosine to give four stereoisomeric exocyclic propano adducts. The
