RING-NITROGEN OF BETA-ISOXAZOLINONE-ALANINE IS INCORPORATED INTO THE NEUROTOXIN, BETA-N-OXALYL-L-ALPHA,BETA-DIAMINOPROPIONIC ACID, IN CALLUS-TISSUE OF LATHYRUS-SATIVUS
Yh. Kuo et al., RING-NITROGEN OF BETA-ISOXAZOLINONE-ALANINE IS INCORPORATED INTO THE NEUROTOXIN, BETA-N-OXALYL-L-ALPHA,BETA-DIAMINOPROPIONIC ACID, IN CALLUS-TISSUE OF LATHYRUS-SATIVUS, Phytochemistry, 37(3), 1994, pp. 713-715
The biosynthesis of beta-N-oxalyl-L-alpha,beta-diaminopropionic acid (
ODAP), the neurotoxin of the grass pea, Lathyrus sativus, was studied
in habituated call-us tissue derived from L. sativus leaves. Chemicall
y synthesized beta-(isoxazolin-5-on-2-yl)-alanine containing the stabl
e isotopes N-15 or C-13 in the ring, or N-15 labelled beta-N-hydroxy-L
-alpha,beta-diaminopropionic acid (HDAP) was used as precursor. The ni
trogen of the isoxazolinone ring is found to be quantitatively incorpo
rated into ODAP, while the carbons of the same ring do not become part
of the ODAP molecule. Also, the beta-amino group of HDAP becomes inco
rporated, suggesting that this compound may be a shortlived intermedia
te.