[26] Aromatic thioethers of purine nucleotides

Publisher Summary Modification of the SH-group of 6-mercaptopurine by suitable substituents results in strong activation of the thioether bonds. A family of substances has been used to attach a covalent label to amino acid side chains, preferentially to the SH group. The reaction proceeds to a cleavage of the aromatic thioether with liberation of a thiophenol. The carbon-6 of the purine is bound to the amino acid side chain although, in some cases, the nitrophenyl moiety is transferred onto the protein. The chapter explains the preparation of S-(Dinitrophenyl)-6-mercaptopurine riboside triphosphate, synthesis of S- (Nitro-4-carboxyphenyl) -6-mercaptopurine riboside 5'-monophosphate, related compounds, and binding of other proteins.