E. Leete
Sep 1, 1977
Citations
0
Influential Citations
32
Citations
Journal
Bioorganic Chemistry
Abstract
Abstract [5,6-14C,13C2]Nicotinic acid was prepared from [14C,13C]methyl iodide via nitromethane, 2-nitroacetaldehyde oxime, 3-nitroquinoline, 3-aminoquinoline, and quinoline in 20% overall yield. Administration of this material to Nicotiana tabacum and N. glauca afforded labeled anabasine, anatabine, nicotine, and nornicotine. Qualitative and quantitative incorporation (0.07–4.5% specific incorporation) was determined by radioactive assay and by examination of the 13C NMR spectra of these alkaloids. Satellites due to spin-spin coupling of the incorporated contiguous 13C atoms were observed at the resonances due to C-5 and C-6 in anabasine, nicotine, and nornicotine. In anatabine, satellites were found at C-5, C-6, C-5′, and C-6′.