89408-81-1Relevant articles and documents
The first stereoselective total synthesis of the Z-isomer of cytospolide e
Yadav,Pandurangam,Suman Kumar,Adi Narayana Reddy,Prasad,Reddy, B.V. Subba,Rajendraprasad,Kunwar
, p. 6048 - 6050 (2012/11/07)
A convergent and highly stereoselective total synthesis of the Z-isomer of cytospolide E has been achieved via Evan's aldol reaction, Sharpless kinetic resolution and RCM cyclisation.
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.