Design of novel conformationally restricted analogues of glutamic acid

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Design of novel conformationally restricted analogues of glutamic acid. / Conti, Paola; De Amici, Marco; Roda, Gabriella; Vistoli, Giulio; Stensbøl, Tine Bryan; Bräuner-Osborne, Hans; Madsen, Ulf; Toma, Lucio; De Micheli, Carlo.

In: Tetrahedron, Vol. 59, No. 9, 24.02.2003, p. 1443-1452.

Research output: Contribution to journal › Journal article › Research › peer-review

Harvard

Conti, P, De Amici, M, Roda, G, Vistoli, G, Stensbøl, TB, Bräuner-Osborne, H, Madsen, U, Toma, L & De Micheli, C 2003, 'Design of novel conformationally restricted analogues of glutamic acid', Tetrahedron, vol. 59, no. 9, pp. 1443-1452. https://doi.org/10.1016/S0040-4020(03)00079-6

APA

Conti, P., De Amici, M., Roda, G., Vistoli, G., Stensbøl, T. B., Bräuner-Osborne, H., Madsen, U., Toma, L., & De Micheli, C. (2003). Design of novel conformationally restricted analogues of glutamic acid. Tetrahedron, 59(9), 1443-1452. https://doi.org/10.1016/S0040-4020(03)00079-6

Vancouver

Conti P, De Amici M, Roda G, Vistoli G, Stensbøl TB, Bräuner-Osborne H et al. Design of novel conformationally restricted analogues of glutamic acid. Tetrahedron. 2003 Feb 24;59(9):1443-1452. https://doi.org/10.1016/S0040-4020(03)00079-6

Author

Conti, Paola ; De Amici, Marco ; Roda, Gabriella ; Vistoli, Giulio ; Stensbøl, Tine Bryan ; Bräuner-Osborne, Hans ; Madsen, Ulf ; Toma, Lucio ; De Micheli, Carlo. / Design of novel conformationally restricted analogues of glutamic acid. In: Tetrahedron. 2003 ; Vol. 59, No. 9. pp. 1443-1452.

Bibtex

@article{6539fca3dba3498b80426e3af39238d6,
title = "Design of novel conformationally restricted analogues of glutamic acid",
abstract = "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.",
keywords = "1,3-dipolar cycloaddition, Bicyclic amino acids, Glutamic acid analogues, Ionotropic glutamate receptors, Metabotropic glutamate receptors",
author = "Paola Conti and {De Amici}, Marco and Gabriella Roda and Giulio Vistoli and Stensb{\o}l, {Tine Bryan} and Hans Br{\"a}uner-Osborne and Ulf Madsen and Lucio Toma and {De Micheli}, Carlo",
note = "Funding Information: This work was financially supported by MIUR (COFIN 2001) Rome and Universit{\`a} 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.",
year = "2003",
month = feb,
day = "24",
doi = "10.1016/S0040-4020(03)00079-6",
language = "English",
volume = "59",
pages = "1443--1452",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Pergamon Press",
number = "9",

}

RIS

TY - JOUR

T1 - Design of novel conformationally restricted analogues of glutamic acid

AU - Conti, Paola

AU - De Amici, Marco

AU - Roda, Gabriella

AU - Vistoli, Giulio

AU - Stensbøl, Tine Bryan

AU - Bräuner-Osborne, Hans

AU - Madsen, Ulf

AU - Toma, Lucio

AU - De Micheli, Carlo

N1 - 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.

PY - 2003/2/24

Y1 - 2003/2/24

N2 - 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.

AB - 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.

KW - 1,3-dipolar cycloaddition

KW - Bicyclic amino acids

KW - Glutamic acid analogues

KW - Ionotropic glutamate receptors

KW - Metabotropic glutamate receptors

UR - http://www.scopus.com/inward/record.url?scp=0037463473&partnerID=8YFLogxK

U2 - 10.1016/S0040-4020(03)00079-6

DO - 10.1016/S0040-4020(03)00079-6

M3 - Journal article

AN - SCOPUS:0037463473

VL - 59

SP - 1443

EP - 1452

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 9

ER -

ID: 379295970