Biosynthesis of echinulin. The stereochemistry of aromatic isoprenylation
- 1 January 1979
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 6,p. 280-282
- https://doi.org/10.1039/c39790000280
Abstract
The incorporation of [1,2-13C]acetate into echinulin has shown that the aromatic isoprenylation at the 5- and 7-positions occurs without any change in stereochemistry around the double bond of the dimethyl-allyl group and chemical degradation of echinulin, obtained by feeding [5(R)-3H]- and [5(S)-3H]mevalonate, to isopentylamine and oxidation with pea seedling diamine oxidase has shown that the isoprenylation reactions at positions 5- and 7- proceed with inversion of configuration at the allylic pyrophosphate.This publication has 4 references indexed in Scilit:
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- Biosynthesis of mycophenolic acid. Substrate stereochemistry of farnesyl pyrophosphate: 5,7-dihydroxy-4-methylphthalide farnesyl transferase from Penicillium brevicompactumJournal of the Chemical Society, Chemical Communications, 1977
- Pattern of incorporation of leucine samples asymmetrically labelled with 13C in the isopropyl unit into the C5-isoprenoid units of echinuline and flavoglaucineJournal of the Chemical Society, Chemical Communications, 1977
- Studies of enzyme-mediated reactions. Part VI. Stereochemical course of the dehydrogenation of stereospecifically labelled benzylamines by the amine oxidase from pea seedlings (E.C. 1.4.3.6.)Journal of the Chemical Society, Perkin Transactions 1, 1976