Biosynthesis of the lupine alkaloids. I. Lupinine Academic Article uri icon

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abstract

  • The mode of incorporation into lupinine of cadaverine, intramolecularly doubly labelled with,15N and with,13C at the C-atom adjacent to 15N, i.e., 13C, 15N-"bond-labelled", was determined by,13C nmr spectroscopy; lupinine is generated from two cadaverine-derived C5-units by a route which excludes a "dimeric" intermediate with C2v symmetry. The mode of incorporation of 2H from L-(2-2H)lysine, from (R)- and (S)-(1-2H)cadaverine, and from (2-2H)-Δ1-piperideine into lupinine was determined by 2H nmr spectroscopy. The results corroborate the conclusions from the 13C,15N experiment and they establish the stereochemistry of six of the steps in the biosynthetic conversion of L-lysine into lupinine.

publication date

  • October 1, 1985