52420-80-1Relevant academic research and scientific papers
Application of (13)C N.M.R. Spectroscopy to Study the Biosynthesis of the Quinolizidine Alkaloids Lupinine and Sparteine
Rana, Jatinder,Robins, David J.
, p. 1133 - 1138 (2007/10/02)
The labelling patterns in (-)-sparteine (14) and (-)-lupinine (15) derived biosynthetically from cadaverine dihydrochloride (13) have been established by (13)C n.m.r. spectroscopy.Three units of (13) are incorporated to about the same extent into sparteine, and two (13)C-(15)N doublets are observed in the (13)C n.m.r. spectrum of sparteine, demonstrating that two of these cadaverine units are converted into the outer rings of sparteine in a specific fashion.Two cadaverine (13) units are incorporated into lupinine (15) and one (13)C-(15)N doublet is observed.These results, and (14)C-labelling experiments with 1,7,13-triazatridecane (10) indicate that a later C5-N-C5 intermediate with C2v symmetry, such as (10), is not involved in lupinine or sparteine biosynthesis.
