title: Radiochemical synthesis of DL-canaline and the colorimetric assay of canaline.
abstract: A procedure is available for the production of DL-[carboxy-14C]canaline from [14C]cyanide by reaction of ethyl N-hydroxyacetimidate and acrolein to form ethyl N-[3-oxopropoxy]acetimidate. The reaction product is converted to the nitrile and then to the hydantoin derivative of DL-canaline; alkaline hydrolysis produces the free amino acid (2-amino-4-aminooxypropionic acid). This procedure can be extended to the production of DL-[carboxy-14C]canavanine by guanidination of C-1-labeled DL-canaline with O-methylisourea. A markedly improved colorimetric assay for canaline has been achieved by a procedure involving carbamylation of canaline with cyanate to form O-ureidohomoserine (2-amino-4-ureidooxybutyric acid). Colorimetric analysis of the latter amino acid markedly enhances the sensitivity, reproducibility, and accuracy of the analysis of L-canaline from biological materials.
mesh_terms: D000613:Aminobutyrates / Q000032:analysis / Q000138:chemical synthesis*; D000818:Animals; D002247:Carbon Isotopes; D003124:Colorimetry; D007887:Fabaceae / Q000032:analysis; D007553:Isotope Labeling; D010946:Plants, Medicinal; D011854:Radiochemistry; D051381:Rats
chemical_list: D000613:Aminobutyrates; D002247:Carbon Isotopes; C001926:canaline