146029-61-0Relevant articles and documents
Structure Elucidation of Monatin, a High-intensity Sweetener Isolated from the Plant Schlerochiton ilicifolius
Vleggaar, Robert,Ackerman, Louis G. J.,Steyn, Pieter S.
, p. 3095 - 3098 (2007/10/02)
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.