Condensation of triformylmethane with adenosine: novel cyclic adducts derived from 1,3-dicarbonyl compounds




Neuvonen K, Koissi N, Lonnberg H

PublisherROYAL SOC CHEMISTRY

2002

Journal of the Chemical Society, Perkin Transactions 2

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2

J CHEM SOC PERK T 2

1

173

177

5

1472-779X

DOIhttps://doi.org/10.1039/b104790f



Condensation of triformylmethane (TFM) with adenosine has been studied in pyridine and aqueous dioxane. One 1:1 (2) and two 2:1 (6 and 7) TFM-adenosine adducts were isolated. The structural assignment of these products by H-1 and C-13 NMR and UV spectroscopy and MS spectrometry suggested that the appearance of the 2:1 adducts is connected to a competitive self-condensation of TFM, the stable end product of which is benzene-1,3,5-tricarbaldehyde. The intermediates on the reaction pathway can be reacted with adenosine affording a new procedure for nucleic acid base modification. The mechanisms of formation and the roles of intramolecular hydrogen bonding in stabilization of cyclic adenosine adducts are discussed.



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