Condensation of triformylmethane with guanosine.

Koissi, N; Neuvonen, K; Munter, T; Kronberg, L; Lönnberg, H

Koissi, N; Neuvonen, K; Munter, T; Kronberg, L; Lönnberg, H.

Afiliación

Koissi N; Department of Chemistry, University of Turku, Finland.

Nucleosides Nucleotides Nucleic Acids ; 20(10-11): 1761-74, 2001.

Article en En | MEDLINE | ID: mdl-11719990

RESUMEN

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).

Asunto(s)

Guanosina/química; Malondialdehído/química; Metano/química; Cromatografía Líquida de Alta Presión; Aductos de ADN; Malondialdehído/análogos & derivados; Modelos Químicos; Ácidos Nucleicos/síntesis química; Espectrofotometría; Factores de Tiempo

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Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Guanosina / Malondialdehído / Metano Tipo de estudio: Prognostic_studies Idioma: En Revista: Nucleosides Nucleotides Nucleic Acids Asunto de la revista: BIOQUIMICA Año: 2001 Tipo del documento: Article País de afiliación: Finlandia Pais de publicación: Estados Unidos

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