title: Synthesis and mutagenicity of the two stereoisomers of an azide metabolite (azidoalanine).
abstract: The L- and D-isomers of azidoalanine (azide metabolite) have been chemically synthesized with 60% yield using corresponding N-(tert-butoxycarbonyl)-serine as starting materials. The mutagenic properties of synthesized L-azidoalanine are very similar to those of azide and in vivo synthesized azidoalanine. Synthetic D-azidoalanine shows very low mutagenic activity on Salmonella typhimurium TA1530 strain compared to that of the L-isomer. Thus a stereoselective process is involved in azidoalanine mutagenicity. The data presented in this study suggest that further biochemical activation is required for L-azidoalanine to produce its mutagenic activity.
mesh_terms: D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification / Q000494:pharmacology; D001386:Azides / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D007202:Indicators and Reagents; D009152:Mutagenicity Tests; D009153:Mutagens / Q000138:chemical synthesis*; D009154:Mutation; D012486:Salmonella typhimurium / Q000187:drug effects; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D001386:Azides; D007202:Indicators and Reagents; D009153:Mutagens; C039309:azidoalanine; D000409:Alanine