Synthesis and mutagenicity of the two stereoisomers of an azide metabolite (azidoalanine)

Add time:07/20/2019    Source:sciencedirect.com

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.

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