1987
DOI: 10.1139/v87-026
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Biosynthesis of lupanine: incorporation of [3,3-2H2]cadaverine

Abstract: . Can. J. Chem. 65, 170 (1987). The mode of incorporation of 2~ from [3,3-2~2]cadaverine into lupanine (2) and 13a-hydroxylupanine (3) in Lupinus angustifolius was determined by 2~ nmr spectroscopy. Lupanine carried deuterium at positions 4a, 4P, 8a, 8P, 13a, and 13P. These six sites were approximately equally enriched. Similarly, 13a-hydroxylupanine carried label approximately equally at five sites, 4a, 4P, 8a, 8P, and 13P. [Traduit par la revue]

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Cited by 8 publications
(10 citation statements)
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“…This biogenetic model also accounts for the stereochemistry of the alkaloids. The model is entirely consistent with the more recent results on the incorporation of I3C and l3C,I5~-labelled (1-5) and 2~-labelled (3,(18)(19)(20)(21) substrates, which are summarized in the introduction. These results define the regiochemistry and the prochirality of biosynthesis.…”
Section: Discussionsupporting
confidence: 89%
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“…This biogenetic model also accounts for the stereochemistry of the alkaloids. The model is entirely consistent with the more recent results on the incorporation of I3C and l3C,I5~-labelled (1-5) and 2~-labelled (3,(18)(19)(20)(21) substrates, which are summarized in the introduction. These results define the regiochemistry and the prochirality of biosynthesis.…”
Section: Discussionsupporting
confidence: 89%
“…The evidence suggests that lysine, C6N2, via cadaverine, 'On leave from the Department of Chemistry, University of Warsaw, 02-093 Warsaw, Poland. Incorporation studies with deuterium-labelled samples of lysine (3) and cadaverine (3,(18)(19)(20)(21) into (-)sparteine (3, 18, 21) (I), (+)sparteine (19) (the enantiomer of I), (+)lupanine (3,18,20,21) 2, and (+)-13a-hydroxylupanine (20,21) (3) throw light on the mode of incorporation of the C5N unit and define the stereochemistry of some of the steps in the biosynthetic sequence from lysine into cadaverine and thence into the alkaloids.…”
Section: Introductionmentioning
confidence: 99%
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“…We set out to prepare sparteine ( l a ) deuteriated at C8 in order to unambiguously assign the resonances for the axial and equatorial protons at this site, which was expected to be labelled by incorporation of cadaverine-3,3-d2 (3). To this end, we undertook a study of the homoenolization of 17-oxosparteine (lb) to establish whether deuterium could be incorporated at C8, P to the lactam carbonyl group.…”
mentioning
confidence: 99%