A1 Refereed original research article in a scientific journal
Condensation of triformylmethane with adenosine: novel cyclic adducts derived from 1,3-dicarbonyl compounds
Authors: Neuvonen K, Koissi N, Lonnberg H
Publisher: ROYAL SOC CHEMISTRY
Publication year: 2002
Journal: Journal of the Chemical Society, Perkin Transactions 2
Journal name in source: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Journal acronym: J CHEM SOC PERK T 2
Issue: 1
First page : 173
Last page: 177
Number of pages: 5
ISSN: 1472-779X
DOI: https://doi.org/10.1039/b104790f
Abstract
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.
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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