SYNTHESIS OF AVENIC ACID A AND 2'-DEOXYMUGIENIC ACID, AMINO ACIDS POSSESSING AN IRON CHELATING ACTIVITY

Article abstract of DOI:10.1246/cl.1981.909

Avenic acid A (1), an amino acid derivative possessing an iron chelating activity and excreted from the root of Avena sativa L. was synthesized in optically active form by successive reductive coupling of protected L-aspartic β-semialdehyde and L-malic semialdehyde with L-homoserine lactone. 2'-Deoxymugineic acid (2), a related substance was also synthesized by the same method by which the stereostructure of this amino acid derivative was proved to be 2(S), 3'(S),3''(S)-N-<3-(3-hydroxy-3-carboxypropylamino)-3-carboxypropyl>-azetidine-2-carboxylic acid.