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Issue 4, 2015
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Determination of the absolute configuration of phosphinic analogues of glutamate

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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

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Publication details

The article was received on 16 Sep 2014, accepted on 11 Nov 2014 and first published on 11 Nov 2014


Article type: Paper
DOI: 10.1039/C4OB01960A
Citation: Org. Biomol. Chem., 2015,13, 1106-1112
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    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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