Abstract:

Tetrahydrofolate(THF) coenzyme is the methyl source of the methylation for many materials(including the DNA and RNA) in the living body to transfer one carbon unit for the biosynthesis and metabolism. The study on mimicking the characteristics of the THF coenzyme can contribute significantly to our understan-ding of the mechanism of action of the coenzymes themselves and provide a valuable effective reagents for groups transfer reaction for practical utility. Owing to such interests, two kinds of imidazolinium iodides 7 and 8 were prepared as the tetrahydrofolate model compounds at the oxidation level of formate, which reacting with bifunctional nucleophiles led to three or five carbon fragments be transferred completely and compound 7 reacts with monofunctional nucleophiles to afford the products transferred part of three carbon fragments. When the reaction of compound 17 as formaldehyde oxidation levels model compound of THF with amines carried out, the four carbon fragments with nitro were completely transferred. The reduction of model compound 7 was also studied. The procedure have mimicked and expanded the function of biochemical transfer of one carbon fragment of the tetrahydrofolate coenzyme and produced some new synthesis methods and reagents which can be applied to organic synthesis.

Key words: Tetrahydrofolate coenzyme, Imidazolinium salt, Transfer reaction, Model