Structure elucidation of monatin, a high-intensity sweetener isolated from the plant Schlerochiton ilicifolius
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 22,p. 3095-3098
- https://doi.org/10.1039/p19920003095
Abstract
The structure of monatin, a high-intensity sweetener isolated from Schlerochiton ilicifolius was elucidated by 1H and 13C NMR spectroscopy as 4-hydroxy-4-(indol-3-ylmethyl)glutamic acid. The 2R*,4R* relative configuration of the two chiral centres in monatin was determined by NOE studies on a derivative, methyl 2-(indol-3-ylmethyl)-4-(2,4-dinitroanilino)-5-oxo-2,3,4,5-tetrahydrofuran-2-carboxylate. The assignment of the 2S configuration to monatin, through application of the Clough–Lutz–Jirgenson rule, established the 2S,4S configuration for the compound.Keywords
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