Canaline is 5-oxa-derivative of ornithine, the only naturally occurring amino acid with an O-alkyl hydroxylamine side chain. It is produced by arginase from Canavanine (the 5-oxa-derivative of arginine). These rare amino acids are produced by legumes such as the jack bean (Canavalia ensiformis) and the alfalfa plant (Medicago sativa) as protective agents against herbivores.

The toxicity of L-Canaline (L-Can) is caused by its ability to form oximes with carbonyl-containing biomolecules such as pyridoxal phosphate, and by its inhibitory effect on ornithine aminotransferase at very low concentrations (10 nM). L-Canaline has also been found to possess antineoplastic and antimalarial properties.

L-Canavanine (L-Cav) is toxic to many herbivores since it is incorporated into their proteins instead of L-Arg, which often leads to structural aberrations and thus to loss of protein function. Moreover, L-Canavanine possesses antitumor activity against human acute leukemia T-cells, and has been of significant interest in cancer research.

Our Fmoc building blocks of L-Can and L-Cav are suitable for SPPS and can be employed in the synthesis of novel peptides.

→ Do you require another building block with an unusual side chain? Our Custom Synthesis team will be happy to provide you with a noncommittal quote.

• L-Canaline: A potent antimetabolite and anti-cancer agent from leguminous plants; G. A. Rosenthal; Life Sciences 1997; 60: 1635-1641. doi:http://dx.doi.org/10.1016/S0024-3205(96)00595-4
• Antimalarial Activities of Aminooxy Compounds; B. J. Berger; Antimicrobial Agents and Chemotherapy 2000; 44: 2540-2542. doi:10.1128/aac.44.9.2540-2542.2000
• Peptidsynthetisch interessante Derivate von L-Canalin; K. Barlos, D. Papaioannou and C. Sanida; Liebigs Annalen der Chemie 1986; 1986: 287-291. doi:10.1002/jlac.198619860208
• Metabolism of L-Canavanine and L-Canaline in Leguminous Plants; G. A. Rosenthal; Plant Physiology 1990; 94: 1-3. doi:10.1104/pp.94.1.1
• Oxime formation between alpha-keto acids and L-canaline; A. J. Cooper; Archives of biochemistry and biophysics 1984; 233: 603-10.
• Canavanine augments proapoptotic effects of arginine deprivation in cultured human cancer cells; B. O. Vynnytska, O. M. Mayevska, Y. V. Kurlishchuk, Y. P. Bobak and O. V. Stasyk; Anticancer Drugs 2011; 22: 148-57. doi:10.1097/CAD.0b013e32833e0334
• The mechanism of L-canavanine cytotoxicity: arginyl tRNA synthetase as a novel target for anticancer drug discovery; A. K. Bence and P. A. Crooks; J Enzyme Inhib Med Chem 2003; 18: 383-94. doi:10.1080/1475636031000152277
• Arginine antimetabolite L-canavanine induces apoptotic cell death in human Jurkat T cells via caspase-3 activation regulated by Bcl-2 or Bcl-xL; M. H. Jang, D. Y. Jun, S. W. Rue, K. Han, W. Park and Y. H. Kim; Biochem Biophys Res Commun 2002; 295: 283-8.
• Single amino acid arginine starvation efficiently sensitizes cancer cells to canavanine treatment and irradiation; B. Vynnytska-Myronovska, Y. Bobak, Y. Garbe, C. Dittfeld, O. Stasyk and L. A. Kunz-Schughart; Int J Cancer 2012; 130: 2164-75. doi:10.1002/ijc.26221