A new opine derived from nopaline.
Nopaline (N-[4-[(aminoiminomethyl)amino-]-1S-carboxybutyl]-2R-aminopentanedioic acid and isonopaline (N-[4-[(aminoiminomethyl)amino-1S-carboxybutyl]- 2S-aminopentanedioic acid) have been synthesized and separated by crystallization. In addition, a derivative of each of these compounds that forms spontaneously from the parent compounds under the usual crystallization conditions was isolated and characterized. The chemical properties, elemental analysis, 1H-NMR spectrum, and electrophoretic behavior of the derivative from nopaline are consistent with N-[4-[ (aminoiminomethyl)amino]-1S-carboxybutyl]-2-pyrrolidone-5R-carboxylic acid, also called pyronopaline. The presence of pyronopaline in crown gall tumor tissue and the catabolism of it by the bacterium A. tumefaciens establish it as a new opine.
D001120:Arginine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000302:isolation & purification; D009682:Magnetic Resonance Spectroscopy; D012231:Rhizobium / Q000254:growth & development*; D013329:Structure-Activity Relationship
C008666:nopaline; C038512:pyronopaline; D001120:Arginine