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Hoffmann, R. A wiki for the life sciences where authorship matters. Nature Genetics (2008)
 
 
 
 
 

Leurosine biotransformations: an unusual ring-fission reaction catalyzed by peroxidase.

The dimeric Vinca alkaloid leurosine undergoes an unusual fission of the piperidine ring of the Iboga substructure when reacted with horseradish peroxidase and hydrogen peroxide. A preparative-scale oxidation of leurosine provided 15'-hydroxycatharinine, which was identified by infrared and proton and carbon-13 NMR spectroscopies and high-resolution mass spectrometry. A proposed pathway for the formation of 15'-hydroxycatharinine involves radical and iminium intermediates and cleavages of a putative diol. The enzymatic transformation product is 3 orders of magnitude less active than leurosine or vinblastine in vitro, in inhibiting the polymerization of tubulin.[1]

References

  1. Leurosine biotransformations: an unusual ring-fission reaction catalyzed by peroxidase. Goswami, A., Macdonald, T.L., Hubbard, C., Duffel, M.W., Rosazza, J.P. Chem. Res. Toxicol. (1988) [Pubmed]
 
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