l-Canavanine synthesis by zinc-mediated guanidination of l-canaline with cyanamide
1986; Elsevier BV; Volume: 14; Issue: 2 Linguagem: Inglês
10.1016/0045-2068(86)90025-8
ISSN1090-2120
AutoresAlvydas J. Ozinskas, Gerald A. Rosenthal,
Tópico(s)Plant-based Medicinal Research
ResumoA novel procedure is described for the synthesis of l-canavanine, 2-amino-4-(guanidinooxy)butyric acid, using cyanamide in the presence of zinc cations for guanidination of the copper salt of l-canaline in nearly quantitative yield. [14C]Cyanamide-zinc(II), obtained from the barium salt, is used to prepare l-[guanidinooxy-14C]canavanine in high yield. Application of cyanamide-zinc(II) to the synthesis of isotopically labeled canavanine derivatives is discussed. Improvements are reported in the procedure for guanidination of l-canaline with O-methylisourea.
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