Oxalyl-2,3-diaminopropionic acid

Among the amino acids from Lathyrus are 2,4-diamino-butyric acid (56) (a neurologically active factor) see above), A -oxalyl-2,3-diaminopropionic acid (57) (a potent neurotoxin), 3-cyanoalanine (58) (a neurotoxin), and the 4-gluta-myl derivative of 3-cyanoalanine. The decarboxylation product of 3-cyanoalanine, 3-aminopropionitrile (59), and its 4-glutamyl derivative induce many of the osteolathyritic skeletal abnormalities (Rosenthal, 1991) (Fig. 13.13). 

XXXVII N -Oxalyl-diaminopropionic acid vetchling Lathyrus sativus Fabaceae... 

N.W. Beyene, H. Moderegger and K. Kalcher, Development of an am-perometric biosensor for /i-iV-oxalyl-L-o ,/i-diaminopropionic acid (fl-ODAP), Electroanalysis, 16(4) (2004) 268-274. 

Olney, J.W., Misra, C.H. and Rhee, V. (1976b). Brain and retinal damage from the lathyrus excitotoxin, /3-N-oxalyl-L-ajS-diaminopropionic acid (ODAP). Nature 264 659-661. 

Lakshmanan J and Padmanaban G (1974) Effect of a-oxalyl-L-a, p-diaminopropionic acid on glutamate uptake by synaptosomes Nature 249, 469-471. 

Arti P. Molecular Biology of Neurotoxin P-N-Oxalyl L-a, P-Diaminopropionic Acid (ODAP) Utilizing Gene. Ph.D. Thesis, PG School, lARI, New Delhi, India. 

N -Oxalyl-L-2,3-diaminopropionic acid (57) is derived from 2,3-diaminopropionic acid (69), which, in turn, is derived from asparagine (64) (Fig. 13.13), The oxalyl derivative (57) is a potent neurotoxin found in Lathyrus sativus and certain other legumes. The corresponding. /V -methyl derivative occurs in certain cycads such as Cycas drdnalis (Rosenthal, 1991). 

Consumption of seeds of the genus Lathyrus (Fabaceae) by man and his domestic animals produces a syndrome called lathyrism. Different amino acids produce the two forms of this malady neurolathyrism and osteolathyrism. 3-Aminopropionitrile 0-aminopropionitrile) (59) is the active osteolathyritic factor in Lathyrus species. Several factors are responsible for neurolathyrism. 3-Cyanoalanine (58), its 4-glutamyl derivative, 2,4-diaminobutyric acid (56), and the N-oxalyl derivative of 2,3-diaminopropionic (a,3-diamino-propionic) acid (57) are all known to be involved. These compounds are found primarily in plants of the genus iMth-yrus. 3-Cyanoalanine (58) and its 4-glutamyl derivative are also common in Vida species. Several related series of compounds are found in other members of the Fabaceae. 

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