Journal article
LEUROSINE BIOTRANSFORMATIONS - AN UNUSUAL RING-FISSION REACTION CATALYZED BY PEROXIDASE
Chemical research in toxicology, Vol.1(4), pp.238-242
07/01/1988
DOI: 10.1021/tx00004a009
PMID: 2979738
Abstract
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. © 1988, American Chemical Society. All rights reserved.
Details
- Title: Subtitle
- LEUROSINE BIOTRANSFORMATIONS - AN UNUSUAL RING-FISSION REACTION CATALYZED BY PEROXIDASE
- Creators
- Animesh Goswami - University of IowaTimothy L MacdonaldClaire HubbardMichael W DuffelJohn P N Rosazza
- Resource Type
- Journal article
- Publication Details
- Chemical research in toxicology, Vol.1(4), pp.238-242
- Publisher
- Amer Chemical Soc
- DOI
- 10.1021/tx00004a009
- PMID
- 2979738
- ISSN
- 0893-228X
- eISSN
- 1520-5010
- Number of pages
- 5
- Grant note
- R01CA013786 / NATIONAL CANCER INSTITUTE; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Cancer Institute (NCI) CA-13786-14 / NCI NIH HHS; United States Department of Health & Human Services; National Institutes of Health (NIH) - USA; NIH National Cancer Institute (NCI)
- Language
- English
- Date published
- 07/01/1988
- Academic Unit
- Pharmacy; Pharmaceutical Sciences and Experimental Therapeutics; Medicinal and Natural Products Chemistry
- Record Identifier
- 9984303161002771
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