Condensation of triformylmethane with adenosine: novel cyclic adducts derived from 1,3-dicarbonyl compounds
: Neuvonen K, Koissi N, Lonnberg H
Publisher: ROYAL 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
DOI: https://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.