title: Condensation of triformylmethane with guanosine.
abstract: Guanosine has been reacted with triformylmethane (TFM) in refluxing pyridine. Four different products, 4-7, were isolated by preparative RP-HPLC, and characterized by 1H and 13C NMR and UV spectroscopy and mass spectrometry. One of the products. the cyclic 1:1 adduct 4, is a stable cyclic carbinolamine formed probably by cyclization of the expected aminomethylene derivative 3. Compound 4 then undergoes reversible dehydration to the fully conjugated adduct 5. The appearance of the additional adducts, 6 and 7, suggests that TFM is prone to transformations resulting in the formation of methylenemalonaldehyde (9) and 1,1,3,3-tetraformylpropane (11).
authors.affiliation: Department of Chemistry, University of Turku, Finland.
authors.forename: N
authors.initials: N
authors.lastname: Koissi
authors.forename: K
authors.initials: K
authors.lastname: Neuvonen
authors.forename: T
authors.initials: T
authors.lastname: Munter
authors.forename: L
authors.initials: L
authors.lastname: Kronberg
authors.forename: H
authors.initials: H
authors.lastname: Lönnberg
mesh_terms: D002851:Chromatography, High Pressure Liquid; D018736:DNA Adducts; D006151:Guanosine / Q000737:chemistry*; D008315:Malondialdehyde / Q000031:analogs & derivatives / Q000737:chemistry*; D008697:Methane / Q000737:chemistry*; D008956:Models, Chemical; D009696:Nucleic Acids / Q000138:chemical synthesis; D013053:Spectrophotometry; D013997:Time Factors
chemical_list: D018736:DNA Adducts; D009696:Nucleic Acids; C453719:triformylmethane; D006151:Guanosine; D008315:Malondialdehyde; D008697:Methane