Issue 22, 1992

Structure elucidation of monatin, a high-intensity sweetener isolated from the plant Schlerochiton ilicifolius

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.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1992, 3095-3098

Structure elucidation of monatin, a high-intensity sweetener isolated from the plant Schlerochiton ilicifolius

R. Vleggaar, L. G. J. Ackerman and P. S. Steyn, J. Chem. Soc., Perkin Trans. 1, 1992, 3095 DOI: 10.1039/P19920003095

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