engleski

FERROCENOYL-NUCLEOBASES. THE CHEMISTRY IN DARK AND IN LIGHT

Organometallic nucleobase derivatives correspond to a new generation of conjugates in which metallocenes are linked to the basic structural elements of heredity. Due to their electrophoric and bioactive properties, they are of use in (bio)analytical and medicinal chemistry [1]. The first ferrocenoyl-purines (Figure) were prepared in our laboratory [2]. We observed that these compounds are sensitive to light. When exposed to UV or visible light, the photochemical degradation occurs in solution, with cyclopentadiene and free nucleobase released from the starting structure. In the absence of light, on the contrary, these compounds are very stable, and no decomposition was observed. In polar organic solvents, however, they undergo N7/N9 isomerization until dynamic equilibrium is reached. This transacylation yields a reaction mixture in which both regioisomers are present and no other transformation was noticed for weeks.

ferrocene, nucleobase, rearrangement, photolysis, prodrug

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