Description and references

Naturally occurring, non-protein amino acid; guanidinooxy analog of arginine, q.v. Predominantly found in leguminous plants; serves as nitrogen storage compound and defensive mechanism. Cytotoxic antimetabolite; substrate for arginyl-tRNA synthetase. Isoln from jack bean, Canavalia ensiformis (L.) DC., Leguminosae: M. Kitagawa, T. Tomiyama, J. Biochem. (Tokyo) 11, 265 (1929); from alfalfa and clover: E. A. Bell Biochem. J. 70, 617 (1958) PubMed. Distribution in the plant kingdom: idem, ibid. 75, 618 (1960) PubMed; B. L. Turner, J. B. Harborne, Phytochemistry 6, 863 (1967) DOI. Structure: J. M. Gulland, C. J. O. R. Morris, J. Chem. Soc. 1935, 763 DOI; M. Kitagawa, A. Takani, J. Biochem. (Tokyo) 23, 181 (1936). Synthesis of racemate: D. D. Nyberg, B. E. Christensen, J. Am. Chem. Soc. 79, 1222 (1957) DOI. HPLC determn in plant tissues: C. Oropeza et al., J. Chromatogr. 456, 405 (1988) DOI. Toxicity and pharmacokinetics in rats: D. A. Thomas, G. A. Rosenthal, Toxicol. Appl. Pharmacol. 91, 395 (1987) DOI PubMed. Review of biological properties: G. A. Rosenthal, Q. Rev. Biol. 52, 155-178 (1977) DOI PubMed; of anticancer activity: A. K. Bence, P. A. Crooks, J. Enzyme Inhib. Med. Chem. 18, 383-394 (2003) DOI PubMed; of association with autoimmunity: J. Akaogi et al., Autoimmun. Rev. 5, 429-435 (2006) DOI PubMed.

Properties

Derivative

Derivative