Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids

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Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids. / Meyer, Udo; Bisel, Philippe; Bräuner-Osborne, Hans; Madsen, Ulf; Höfner, Georg; Wanner, Klaus Th; Frahm, August Wilhelm.

In: Chirality, Vol. 17, No. 2, 02.2005, p. 99-107.

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

Harvard

Meyer, U, Bisel, P, Bräuner-Osborne, H, Madsen, U, Höfner, G, Wanner, KT & Frahm, AW 2005, 'Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids', Chirality, vol. 17, no. 2, pp. 99-107. https://doi.org/10.1002/chir.20110

APA

Meyer, U., Bisel, P., Bräuner-Osborne, H., Madsen, U., Höfner, G., Wanner, K. T., & Frahm, A. W. (2005). Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids. Chirality, 17(2), 99-107. https://doi.org/10.1002/chir.20110

Vancouver

Meyer U, Bisel P, Bräuner-Osborne H, Madsen U, Höfner G, Wanner KT et al. Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids. Chirality. 2005 Feb;17(2):99-107. https://doi.org/10.1002/chir.20110

Author

Meyer, Udo ; Bisel, Philippe ; Bräuner-Osborne, Hans ; Madsen, Ulf ; Höfner, Georg ; Wanner, Klaus Th ; Frahm, August Wilhelm. / Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids. In: Chirality. 2005 ; Vol. 17, No. 2. pp. 99-107.

Bibtex

@article{7b3d7bb96df248abaf5083238edc2bf3,
title = "Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids",
abstract = "The second-generation asymmetric synthesis of the trans-tris(homoglutamic) acids reported herein proceeds via Strecker reaction of chiral ketimines, obtained from condensation of racemic 2-ethoxycarbonylmethylcyclopentanone and commercially available (S)- and (R)-1-phenylethylamine, respectively. In the key stereodifferentiating step, the cyanide addition leads to mixtures of diastereomeric alpha-amino nitrile-esters, the composition of which is independent of the reaction temperature and the type of the solvent, respectively. Hydrolysis of the alpha-amino nitrile-esters with concentrated H(2)SO(4) yielded diastereomeric mixtures of secondary alpha-amino amido-esters, which after separation were hydrogenolyzed and hydrolyzed each to the enantiomeric trans-1-amino-2-carboxymethylcyclopentanecarboxylic acids. Their configuration was completely established by NMR methods, CD spectra, and X-ray analysis of the trans-1S,2R-configured secondary alpha-amino amido-ester. In receptor binding assays and functional tests, trans-1S,2R-1-amino-2-carboxymethylcyclopentanecarboxylic acid hydrochloride was found to behave as a selective mGluR(2)-antagonist without relevant binding properties at iGluRs.",
keywords = "Amino Acids, Cyclic, Glutamic Acid, Ligands, Molecular Structure, Receptors, Glutamate, Stereoisomerism, Thermodynamics",
author = "Udo Meyer and Philippe Bisel and Hans Br{\"a}uner-Osborne and Ulf Madsen and Georg H{\"o}fner and Wanner, {Klaus Th} and Frahm, {August Wilhelm}",
note = "Copyright 2005 Wiley-Liss, Inc.",
year = "2005",
month = feb,
doi = "10.1002/chir.20110",
language = "English",
volume = "17",
pages = "99--107",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley",
number = "2",

}

RIS

TY - JOUR

T1 - Rigid nonproteinogenic cyclic amino acids as ligands for glutamate receptors: trans-tris(homoglutamic) acids

AU - Meyer, Udo

AU - Bisel, Philippe

AU - Bräuner-Osborne, Hans

AU - Madsen, Ulf

AU - Höfner, Georg

AU - Wanner, Klaus Th

AU - Frahm, August Wilhelm

N1 - Copyright 2005 Wiley-Liss, Inc.

PY - 2005/2

Y1 - 2005/2

N2 - The second-generation asymmetric synthesis of the trans-tris(homoglutamic) acids reported herein proceeds via Strecker reaction of chiral ketimines, obtained from condensation of racemic 2-ethoxycarbonylmethylcyclopentanone and commercially available (S)- and (R)-1-phenylethylamine, respectively. In the key stereodifferentiating step, the cyanide addition leads to mixtures of diastereomeric alpha-amino nitrile-esters, the composition of which is independent of the reaction temperature and the type of the solvent, respectively. Hydrolysis of the alpha-amino nitrile-esters with concentrated H(2)SO(4) yielded diastereomeric mixtures of secondary alpha-amino amido-esters, which after separation were hydrogenolyzed and hydrolyzed each to the enantiomeric trans-1-amino-2-carboxymethylcyclopentanecarboxylic acids. Their configuration was completely established by NMR methods, CD spectra, and X-ray analysis of the trans-1S,2R-configured secondary alpha-amino amido-ester. In receptor binding assays and functional tests, trans-1S,2R-1-amino-2-carboxymethylcyclopentanecarboxylic acid hydrochloride was found to behave as a selective mGluR(2)-antagonist without relevant binding properties at iGluRs.

AB - The second-generation asymmetric synthesis of the trans-tris(homoglutamic) acids reported herein proceeds via Strecker reaction of chiral ketimines, obtained from condensation of racemic 2-ethoxycarbonylmethylcyclopentanone and commercially available (S)- and (R)-1-phenylethylamine, respectively. In the key stereodifferentiating step, the cyanide addition leads to mixtures of diastereomeric alpha-amino nitrile-esters, the composition of which is independent of the reaction temperature and the type of the solvent, respectively. Hydrolysis of the alpha-amino nitrile-esters with concentrated H(2)SO(4) yielded diastereomeric mixtures of secondary alpha-amino amido-esters, which after separation were hydrogenolyzed and hydrolyzed each to the enantiomeric trans-1-amino-2-carboxymethylcyclopentanecarboxylic acids. Their configuration was completely established by NMR methods, CD spectra, and X-ray analysis of the trans-1S,2R-configured secondary alpha-amino amido-ester. In receptor binding assays and functional tests, trans-1S,2R-1-amino-2-carboxymethylcyclopentanecarboxylic acid hydrochloride was found to behave as a selective mGluR(2)-antagonist without relevant binding properties at iGluRs.

KW - Amino Acids, Cyclic

KW - Glutamic Acid

KW - Ligands

KW - Molecular Structure

KW - Receptors, Glutamate

KW - Stereoisomerism

KW - Thermodynamics

U2 - 10.1002/chir.20110

DO - 10.1002/chir.20110

M3 - Journal article

C2 - 15660439

VL - 17

SP - 99

EP - 107

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 2

ER -

ID: 45613574