Design of novel conformationally restricted analogues of glutamic acid
Research output: Contribution to journal › Journal article › Research › peer-review
Stereomeric 3-carboxy-Δ2-isoxazoline-cyclopentane amino acids, which represent restricted conformations of glutamic acid, have been prepared through a strategy based on the 1,3-dipolar cycloaddition of ethoxycarbonylformonitrile oxide to a suitably protected 1-amino-cyclopent-2-enecarboxylic acid. These amino acids, assayed at iGluRs and mGluRs, proved to be inactive. The biological data have been accounted for through the comparison of their conformational profile with that of a 3-carboxy-Δ2-isoxazolinyl proline (CIP-A) and (±)-1-aminocyclopentane-1,3-dicarboxylic acid.
| Original language | English |
|---|---|
| Journal | Tetrahedron |
| Volume | 59 |
| Issue number | 9 |
| Pages (from-to) | 1443-1452 |
| Number of pages | 10 |
| ISSN | 0040-4020 |
| DOIs | |
| Publication status | Published - 24 Feb 2003 |
Bibliographical note
Funding Information:
This work was financially supported by MIUR (COFIN 2001) Rome and Università degli Studi di Milano. The financial support to H. B. O. by the Danish Medical Research Council, the Novo Nordisk Foundation, the Augustinus Foundation and Ib Henriksens Foundation is grateful acknowledged.
- 1,3-dipolar cycloaddition, Bicyclic amino acids, Glutamic acid analogues, Ionotropic glutamate receptors, Metabotropic glutamate receptors
Research areas
ID: 379295970