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

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

Bioorg Chem

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

Published: February 2006

AI Article Synopsis

  • Treatment of 2'-deoxyadenosine with acrolein at a specific temperature and pH creates unstable adducts with one or two fused ring systems.
  • The reaction using 2'-deoxyadenosine produces at least four different diastereoisomers, complicating product identification.
  • To simplify the analysis, 9-ethyladenine was used instead, and the products were characterized through UV, mass spectrometry, and NMR spectroscopy.

Article Abstract

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.

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Source
http://dx.doi.org/10.1016/j.bioorg.2005.10.006DOI Listing

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