Stereocontrolled syntheses of all four stereoisomeric 1,N2-deoxyguanosine adducts of the lipid peroxidation product trans-4-hydroxynonenal.
[structure: see text]. trans-4-hydroxynonenal (4-HNE) is a unique product from the peroxidation of omega-6 polyunsaturated fatty acids. The major reaction of racemic 4-HNE with DNA is with deoxyguanosine to give four stereoisomeric exocyclic propano adducts. The stereospecific syntheses of these four adducts has been achieved at the nucleoside level. The synthetic approach is amenable to the synthesis of structurally defined oligonucleotides containing these endogenous genotoxins.
Wang
H
H
Department of Chemistry and Center in Molecular Toxicology, Vanderbilt University, VU Station B 351822, Nashville, Tennessee 37235-1822, USA.
Rizzo
C J
CJ
D000447:Aldehydes / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D018736:DNA Adducts / Q000138:chemical synthesis; D003849:Deoxyguanosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D015227:Lipid Peroxidation; D009682:Magnetic Resonance Spectroscopy; D009153:Mutagens / Q000138:chemical synthesis*; D013237:Stereoisomerism
D000447:Aldehydes; D018736:DNA Adducts; D009153:Mutagens; D003849:Deoxyguanosine; C027576:4-hydroxy-2-nonenal