Reaction of acrolein with 2'-deoxyadenosine and 9-ethyladenine--formation of cyclic adducts.
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.
Pawłowicz
Agnieszka J
AJ
Department of Organic Chemistry, Abo Akademi University, Biskopsgatan 8, FIN-20500 Abo, Finland.
Munter
Tony
T
Klika
Karel D
KD
Kronberg
Leif
L
D000171:Acrolein / Q000737:chemistry*; D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry; D018736:DNA Adducts / Q000737:chemistry*; D003839:Deoxyadenosines / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D008956:Models, Chemical; D013057:Spectrum Analysis; D013237:Stereoisomerism
D018736:DNA Adducts; D003839:Deoxyadenosines; C001172:9-ethyladenine; D000171:Acrolein; D000225:Adenine; C058118:2'-deoxyadenosine