"One-pot" syntheses of malondialdehyde adducts of nucleosides
Jozsef Szekely1, Hao Wang, Katherine M Peplowski
1Department of Chemistry, Center in Molecular Toxicology, Vanderbilt Institute of Chemical Biology and Vanderbilt-Ingram Cancer Center, Vanderbilt University, Nashville, TN 37235-1822, USA.
Abstract:
Short, "one-pot" syntheses of malondialdehyde adducts of deoxyguanosine, deoxyadenosine, and deoxycytidine are described. These syntheses proceed in improved yield and easier purification than previous syntheses and are well suited for the preparation of isotopically labeled nucleoside adducts for biomarker and metabolic studies.
More Related Videos
Related Concept Videos
Alkylation of β-Diester Enolates: Malonic Ester Synthesis
Base-Catalyzed Aldol Addition Reaction
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
Biosynthesis of Nucleic Acids
Conjugate Addition (1,4-Addition) vs Direct Addition (1,2-Addition)
Conjugate addition results in a thermodynamically stable product. The reaction retains the stronger C=O bond at the expense of the weaker C=C π bond. The process is slow as the β carbon is less electrophilic than the carbonyl carbon.
Direct addition products are formed faster owing to...
Conjugate Addition to α,β-Unsaturated Carbonyl Compounds


