Issue 4, 2015

Determination of the absolute configuration of phosphinic analogues of glutamate

Abstract

A series of phosphinic glutamate derivatives (e.g.LSP1-2111) have been proven to be potent agonists of metabotropic glutamate (mGlu) receptors and shown promising in vivo activity. However, so far all were synthesized and tested as a mixture of two diastereomers whose absolute and relative configurations are not known. In this study, the stereomers were separated on a Crownpack CR(+) column and their absolute configuration was assessed by means of a diastereoselective synthesis. Both separated L-stereomers activated the mGlu4 receptor with EC50's of 0.72 and 4.4 μM for (1S,1′S)-and (1S,1′R)-LSP1-2111, respectively.

Graphical abstract: Determination of the absolute configuration of phosphinic analogues of glutamate

Supplementary files

Article information

Article type
Paper
Submitted
16 Sep 2014
Accepted
11 Nov 2014
First published
11 Nov 2014

Org. Biomol. Chem., 2015,13, 1106-1112

Determination of the absolute configuration of phosphinic analogues of glutamate

B. Commare, D. Rigault, I. A. Lemasson, P. Deschamps, A. Tomas, P. Roussel, I. Brabet, C. Goudet, J. Pin, F. R. Leroux, F. Colobert and F. C. Acher, Org. Biomol. Chem., 2015, 13, 1106 DOI: 10.1039/C4OB01960A

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