Portal de Periódicos da CAPES

Ornithine as a precursor for the pyrrolidine ring of nicotine

1959; Elsevier BV; Volume: 33; Issue: 1 Linguagem: Inglês

10.1016/0006-3002(59)90492-5

1878-2434

B.L. Lamberts, Lovell J. Dewey, Richard U. Byerrum,

Molecular Spectroscopy and Structure

Radioactive nicotine, from Nicotiana rustica plants which had been fed [2-14C]-ornithine, was degraded with recovery of C-5 of the pyrrolidine ring. This position of the ring was shown to have about half of the radioactivity of the original nicotine. The remaining radioactivity was in the residual carbon skeleton of the nicotine which was isolated as a derivative of a substituted primary amine. A previous degradation had established that the radioactivity in the amine derivative was in the carbon atom corresponding to position 2 of the pyrrolidine ring of nicotine. This pattern of labelling supports the postulation of one or more symmetrical intermediates in the synthesis of the pyrrolidine ring of nicotine from the amino acid ornithine.