Azetidine-2-carboxylic acid derivatives from seeds of Fagus silvatica L. and a revised structure for nicotianamine |
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Authors: | Ib Kristensen Peder Olesen Larsen |
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Affiliation: | Department of Organic Chemistry, Royal Veterinary and Agricultural University, 40 Thorvaldsensvej, DK- 1871 Copenhagen, Denmark |
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Abstract: | 2(S),3′(S)-N-(3-Amino-3-carboxypropyl)azetidine-2-carboxylic acid and 2(S),3′(S),3″(S)-N-[N-(3-amino-3-carboxypropyl)-3-amino-3-carboxypropyl]azetidine-2-carboxylic acid have been isolated from seeds of Fagus silvatica L. (beechnuts). The structures have been established by PMR- and 13C-NMR-spectroscopy and by synthesis from l-azetidine-2-carboxylic acid. The second of the new amino acids is identical with nicotianamine. previously isolated from Nicotiana tabacum but assigned a different formula. The ring opening reactions of azetidine-2-carboxylic acid in neutral solution have been studied and the chemical and possibly biochemical precursor role of this amino acid for various amino acids including the two new ones described here, nicotianine [N-(3-amino-3-carboxypropyl)nicotinic acid] and methionine is discussed. |
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Keywords: | Fagaceae beechnuts azetidine-2-carboxylic acid nicotianamine non-protein amino acids imino acids. |
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