Synthesis of Nicotianamine and a Related Compound,Derivatives of Azetidine-2-carboxylic Acid

Abstract

The synthesis of nicotianamine (1) and a r e l a t e d compound (2) amino acid derivatives having the azetidine r i n gwas achieved by reductive coupling of L-aspartic-5-semialdehyde derivatives with L-azetidine-2-carboxylic acid methyl ester.Nicotianamine (1) i s a unique amino a c i d containing the azetidine-2-carboxylic acid moiety, f i r s t i s o l a t e d from the leaves of Nicotiana -.''I t s structure was elucidated as 2(S), 7. 5 .Takagi, S o i l Sci.P l a n t N u t r ., g, 423 (1976) 8.