Journal article
Enzymic and chemical oxidations of leurosine to 5'-hydroxyleurosine
Journal of organic chemistry, Vol.52(8), pp.1500-1504
04/01/1987
DOI: 10.1021/jo00384a022
Abstract
The major product obtained when leurosine was oxidized by microorganisms, copper oxidase enzyme systems, benzoquinone, and DDQ has been identified as a mixture of chromatographically inseparable 5'-hydroxyleurosine isomers. The leurosine oxidation product is only one of several possible positional carbinolamine isomers. The precise location of the carbinolamine functionality was clearly determined by carbon-13 NMR spectral analysis of 5'-deuterioleurosine obtained by sodium borodeuteride reduction of the carbinolamine. By virtue of the oxidants employed, it is likely that leurosine is first oxidized to a nitrogen centered cation-radical which loses hydrogen to form an iminium derivative that adds water. The possible occurrence of equilibrium mixtures of isomeric iminium intermediates in the oxidation reaction mixture was excluded by spectral analysis of the product formed when leurosine oxidations were conducted in deuterium oxide
Details
- Title: Subtitle
- Enzymic and chemical oxidations of leurosine to 5'-hydroxyleurosine
- Creators
- Animesh GoswamiJohn P SchaumbergMichael W DuffelJohn P Rosazza
- Resource Type
- Journal article
- Publication Details
- Journal of organic chemistry, Vol.52(8), pp.1500-1504
- Publisher
- American Chemical Society
- DOI
- 10.1021/jo00384a022
- ISSN
- 0022-3263
- eISSN
- 1520-6904
- Language
- English
- Date published
- 04/01/1987
- Academic Unit
- Medicinal and Natural Products Chemistry; Pharmaceutical Sciences and Experimental Therapeutics; Pharmacy
- Record Identifier
- 9984303284702771
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