Stereospecific N-methylation of the tetrahydroisoquinoline alkaloids isosalsoline and salsolidine by amine N-methyltransferase A from bovine liver.

Stereospecific N-methylation of the tetrahydroisoquinoline alkaloids isosalsoline (7-hydroxy-6-methoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) and salsolidine (6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline) by amine N-methyltransferase A isolated from bovine liver is reported. Incubation with S-adenosylmethionine as cosubstrate revealed that in case of isosalsoline, an endogenous tetrahydroisoquinoline alkaloid, the (+)-(R)-enantiomer, is preferentially methylated, whereas in the case of salsolidine the (-)-(S)-enantiomer is preferentially methylated. The results were obtained by using two independent methods, namely a radioassay and HPLC following separate incubation experiments.