Radiochemical synthesis of dl-canaline and the colorimetric assay of canaline

✍ Scribed by Gerald A. Rosenthal; Deborah Thomas

• Publisher: Elsevier Science
• Year: 1984
• Tongue: English
• Weight: 361 KB
• Volume: 140
• Category: Article
• ISSN: 0003-2697
• DOI: 10.1016/0003-2697(84)90160-x

✦ Synopsis

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.