Synthesis and characterisation of a new class of stable S-adenosyl-L-methionine salts

S-adenosyl-L-methionine (SAM) is an important metabolic intermediate that s erves as a donor of methyl and aminopropyl groups to a variety of acceptor molecules. The molecule in vitro is unstable both in solution and in crysta lline form undergoing irreversible conversion to 5'-methyltioadenosine (MTA ) and homoserine lactone. Since this form of instability stems to bt: preve nted in the cell of the living organism by bonds with macromolecules, we de signed and developed a novel class of salts of SAM with large size anions t o improve the stability of the sulfonium compound outside the cell. For thi s purpose we synthesised and characterised by NMR and IR spectroscopy anion s consisting of amidic derivatives of taurine with fatty acids. Stability s tudies performed with the new SAM sails indicate that SAM becomes much more stable when it interacts with large size anions and in fact more than 84%; of the SAM is recovered after 36 months in lyophilized samples. The high s tability of the new products widens the possibility of new; therapeutic app lications of SAM in human therapy. (C) 2000 Elsevier Science B.V. All right s reserved.