A1 Refereed original research article in a scientific journal
Reactions of adenosine with bromo- and chloromalonaldehydes in aqueous solution: Kinetics and mechanism
Authors: Mikkola S, Koissi N, Ketomaki K, Rauvala S, Neuvonen K, Lonnberg H
Publisher: WILEY-V C H VERLAG GMBH
Publication year: 2000
Journal: European Journal of Organic Chemistry
Journal name in source: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Journal acronym: EUR J ORG CHEM
Issue: 12
First page : 2315
Last page: 2323
Number of pages: 9
ISSN: 1434-193X
Abstract
Reactions of adenosine nucleosides with halogen substituted acetaldehydes and malonaldehydes have been studied and pseudo first-order rate constants have been determined. All the reactions yield 1,N-6-etheno adducts, and with malonaldehydes, in addition to this, 11-formyl-1,N-6-etheno adducts are also formed. Particular attention has been paid to the formation of the formyletheno products. The results obtained suggest that the reactions of adenine base with halogenated acetaldehydes and malonaldehydes are basically similar. It also seems that in reactions of halomalonaldehydes with adenosine, the etheno and formyletheno products are formed through the same initial reaction pathway i. e. the attack of the B-amino group of the adenine base at the carbonyl carbon atom of the aldehyde.
Reactions of adenosine nucleosides with halogen substituted acetaldehydes and malonaldehydes have been studied and pseudo first-order rate constants have been determined. All the reactions yield 1,N-6-etheno adducts, and with malonaldehydes, in addition to this, 11-formyl-1,N-6-etheno adducts are also formed. Particular attention has been paid to the formation of the formyletheno products. The results obtained suggest that the reactions of adenine base with halogenated acetaldehydes and malonaldehydes are basically similar. It also seems that in reactions of halomalonaldehydes with adenosine, the etheno and formyletheno products are formed through the same initial reaction pathway i. e. the attack of the B-amino group of the adenine base at the carbonyl carbon atom of the aldehyde.
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