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Crystal structure of cis-2-(2-carboxycyclopropyl)glycine (CCG-III) monohydrate
oleh: Sergey Lindeman, Nathaniel J. Wallock, William A. Donaldson
Format: | Article |
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Diterbitkan: | International Union of Crystallography 2015-07-01 |
Deskripsi
The title compound, C6H9NO4·H2O [systematic name: (αR,1R,2S)-rel-α-amino-2-carboxycyclopropaneacetic acid monohydrate], crystallizes with two organic molecules and two water molecules in the asymmetric unit. The space group is P21 and the organic molecules are enantiomers, thus this is an example of a `false conglomerate' with two molecules of opposite handedness in the asymmetric unit (r.m.s. overlay fit = 0.056 Å for one molecule and its inverted partner). Each molecule exists as a zwitterion, with proton transfer from the amino acid carboxylic acid group to the amine group. In the crystal, the components are linked by N—H...O and O—H...O hydrogen bonds, generating (100) sheets. Conformationally restricted glutamate analogs are of interest due to their selective activation of different glutamate receptors, and the naturally occurring (+)-CCG-III is an inhibitor of glutamate uptake and the key geometrical parameters are discussed.