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The biosynthesis of the trisnor sesquiterpenoid geosmin (4,8a-dimethyl-octahydro-naphthalen-4a-ol) (1) was investigated by feeding labeled [5,5- 2 H 2 ]-1-desoxy-d-xylulose (11), [4,4,6,6,6- 2 H 5 ]-mevalolactone (7) and [2,2- 2 H 2 ]-mevalolactone (9) to Streptomyces sp. JP95 and the liverwort Fossombronia pusilla. The micro-organism produced geosmin...
Preincubation of detached leaves of Apium graveolens with deuterium labelled [5,5- 2 H 2 ]-deoxy-d-xylulose prior to the elicitation of furanocoumarin biosynthesis by jasmonic acid, resulted in high incorporation of a deuterated prenyl segment into all genuine furanocoumarins. Psoralen, xanthotoxin, bergapten and iso-pimpinellin consistently showed at C-3' of the furan moiety...
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