Homochiral synthesis of an aza analogue of S-adenosyl-L-methionine (AdoMet) and its binding to the E. coli methionine repressor protein (MetJ)

Abstract

A synthesis of 5′-{N-[(S)-3-amino-3-carboxypropyl]-methylamino}-5′-deoxyadenosine from D-adenosine and (S)-glutamic acid is described; this product, AzaAdoMet 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 repressor protein is investigated by X-ray crystallography.