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Reactions of Adenosine with Bromo‐ and Chloromalonaldehydes in Aqueous Solution: Kinetics and Mechanism
Author(s) -
Mikkola Satu,
Koissi Niangoran,
Ketomäki Kaisa,
Rauvala Susanna,
Neuvonen Kari,
Lönnberg Harri
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200006)2000:12<2315::aid-ejoc2315>3.0.co;2-g
Subject(s) - chemistry , kinetics , aqueous solution , mechanism (biology) , adenosine , organic chemistry , biochemistry , physics , quantum mechanics , philosophy , epistemology
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 6‐amino group of the adenine base at the carbonyl carbon atom of the aldehyde.