A new opine derived from nopaline.

Abstract

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.

• Authors: L M Hall, J L Schrimsher, K B Taylor
• Journal: The Journal of biological chemistry (J Biol Chem) Vol. 258 Issue 12 Pg. 7276-9 (Jun 25 1983) ISSN: 0021-9258 [Print] United States
• PMID: 6863246 (Publication Type: Journal Article, Research Support, U.S. Gov't, P.H.S.)

Chemical References

• nopaline
• pyronopaline
• Arginine

Topics

• Arginine (analogs & derivatives, chemical synthesis, isolation & purification)
• Magnetic Resonance Spectroscopy
• Rhizobium (growth & development)
• Structure-Activity Relationship