Glutamyl Derivatives of Amines

The glutamyl derivatives of amines so far identified in plants are listed in Table 6. Again, information on the occurrence of the free amine in plants together with information on chemical syntheses is included. Unlike amino acids, the amines corresponding to the y-glu-tamyl derivatives have in most cases not been identified in plants. 

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Table 6. y-Glutamyl Derivatives of Amines Identified in Plants... 

In the case of a few y-glutamyl derivatives of non-protein amino acids the parent amino acid has not been found in natural material. Furthermore, with a number of the y-glutamyl derivatives of amines specific problems have been encountered. In these cases a detailed individual discussion is of interest. 

Block, E., Birringer, M., Jiang, W., Nakahodo, T., Thompson, H. J., et al. Allium chemistry synthesis, natural occurence, biological activity, and chemistry of Se-alk(en)ylselenocysteines and their y-glutamyl derivatives and oxidation products. J Agric Food Chem 2001, 49, 458 470. Das, A., Desai, D., Pittman, B., Amin, S., El-Bayoumy, K. Comparison of the chemopreventive efficacies of l,4-phenylenebis(methylene)selenocyanate and selenium-enriched yeast on 4-(methylnitrosamino)-l-(3-pyridyl)-l-butanone induced lung tumorigenesis in A/J mouse. Nutr Cancer 2003, 46, 179-185. 

Compound Formula Plant species Plant family Character of isolate, comments Configuration of Gluta- The mic amine acid moiety Ref. Occurrence of amine Chemical synthesis of y-glutamyl derivative Method Ref. 

In the fifth method p-toluensulphonyl-5-oxo-L-proline is condensed with an amine or an ester of an amino acid with subsequent removal of the p-toluensulphonyl group by the use of sodium in liquid ammonia. Again, the method gives only the y-glutamyl derivative. 

A number of y-glutamyl derivatives from plants are toxic towards animals or have other specific biological actions. In most cases the action is due to the second amino acid or amine, but y-glutamyl derivatives may be of importance if they contain the bulk of the toxic component in the plant material in question. 

Kasai, T., Larsen, P. O. Chemistry and biochemistry of y-glutamyl derivatives from plants including mushrooms (Basidiomycetes). Prog. Chem. Org. Nat. Prod. 39, 173-285 (1980) Leete, E. Alkaloids derived from ornithine, lysine and nicotinic acid. In Encyclopedia of Plant Physiology, New Series, Vol. 8, Secondary Plant Products (E. A. Bell, B. V. Charlwood, eds.), pp. 65-91. Springer, Berlin-Heidelberg-New York 1980 Smith, T. A. Amines. In The Biochemistry of Plants, Vol. 7, Secondary Plant Products (E. E. 

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