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    Bioorg Chem. 2006 Feb;34(1):39-48. Epub 2005 Dec 15.

    Reaction of acrolein with 2'-deoxyadenosine and 9-ethyladenine--formation of cyclic adducts.

    Pawłowicz AJ, Munter T, Klika KD, Kronberg L.

    Department of Organic Chemistry, Abo Akademi University, Biskopsgatan 8, FIN-20500 Abo, Finland.

    Treatment of 2'-deoxyadenosine with acrolein at pH 4.6 in 37 degrees C affords unstable adducts containing either one or two fused ring systems where the hydroxypropano units are derived from acrolein. Since the use of 2'-deoxyadenosine resulted in the creation of at least four diastereoisomers for the adduct made up of two fused rings, therefore, for identification and assignment of the products, 9-ethyladenine was used instead as the starting material in the reaction. The products, 3E and 4E, were structurally characterised by UV, mass spectrometry and NMR spectroscopy.

    PMID: 16343591 [PubMed - indexed for MEDLINE]

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