Condensation of triformylmethane with guanosine.
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).
Koissi
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N
Department of Chemistry, University of Turku, Finland.
Neuvonen
K
K
Munter
T
T
Kronberg
L
L
Lönnberg
H
H
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
D018736:DNA Adducts; D009696:Nucleic Acids; C453719:triformylmethane; D006151:Guanosine; D008315:Malondialdehyde; D008697:Methane