23 鉄キレート活性を有するアミノ酸avenic acid A,Bおよび関連アミノ酸の構造と合成
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Several amino acid derivatives possessing an iron chelating activity have been isolated from the excreta of root of oats cultured under iron deficient conditions. During the course of studies to isolate such amino acid derivatives, avenic acid B 1 was isolated from an ethanol extract from the root of Avena sativa. The structure of this compound was confirmed as 2(S),3'(S)-N-(3-hydroxy-3-carboxypropyl)-homoserine on the basis of nmr analysis and by chemical synthesis. Synthesis of 1 was achieved through reductive coupling of L-malic half-aldehyde derivative 17 to L-homoserine lactone hydrobromide 18 by using of NaBH_3CN, a selective reducing agent, followed by hydrolysis. Avenic acid A, 2(S),3'(S),3"(S)-N-[3-(3-hydroxy-3-carboxypropylamino)-3-carboxypropyl]-homoserine 2, a chelating amino acid isolated from the root washings of Avena sativa was also synthesized in the same way. Reaction of homoserine lactone hydrobromide 18 with L-aspartic-β-semialdehyde 9c gave 20c. Reductive coupling of 22, the decarbobenzoxylation product of 20c and L-malic half-aldehyde derivative 17 yielded avenic acid A after deprotection. Nicotianamine, 2(S),3'(S),3"(S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]-azetidine-2-carboxylic acid 3, an amino acid derivative being widely distributed in Solanumplants and 2(S),3'(S)-N-(3-amino-3-carboxypropyl)-azetidine-2-carboxylic acid 4, isolated from Fagus silvatica L. were also synthesized from L-azetidine-2-carboxylic acid 24 and L-aspartic-β-semialdehyde derivatives (9a, 9c).
- 天然有機化合物討論会の論文
- 1980-09-10
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