HOMOCHIRAL SYNTHESIS OF AN AZA ANALOG OF S-ADENOSYL-L-METHIONINE (ADOMET) AND ITS BINDING TO THE ESCHERICHIA-COLI METHIONINE REPRESSOR PROTEIN (METJ)

A synthesis of ino-3-carboxypropyl]methylamino}-5'-deoxyadenosine from D-adenosine and (S)-glutamic acid is described; this product, AzaAdoM et 2, has a pK(a) of 7.10 for the tertiary amino group and so acts as a charge-switchable analogue of AdoMet 1, a key component of polyamine biosynthesis; the binding of both 1 and 2 to the E. coli methionine r epressor protein is investigated by X-ray crystallography.