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Crystal structure of cis-2-(2-carb-oxy-cyclo-prop-yl)glycine (CCG-III) monohydrate.

Lindeman S, Wallock NJ, Donaldson WA - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: Each mol-ecule exists as a zwitterion, with proton transfer from the amino acid carb-oxy-lic 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 inter-est 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Marquette University, PO Box 1881, Milwaukee, WI 53201-1881, USA.

ABSTRACT
The title compound, C6H9NO4·H2O [systematic name: (αR,1R,2S)-rel-α-amino-2-carb-oxy-cyclo-propane-acetic acid monohydrate], crystallizes with two organic mol-ecules and two water mol-ecules in the asymmetric unit. The space group is P21 and the organic mol-ecules are enanti-omers, thus this is an example of a 'false conglomerate' with two mol-ecules of opposite handedness in the asymmetric unit (r.m.s. overlay fit = 0.056 Å for one mol-ecule and its inverted partner). Each mol-ecule exists as a zwitterion, with proton transfer from the amino acid carb-oxy-lic 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 inter-est 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.

No MeSH data available.


Related in: MedlinePlus

Structures of the diastereomers of 2-(2′-carb­oxy­cyclo­prop­yl)glycine.
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fig1: Structures of the diastereomers of 2-(2′-carb­oxy­cyclo­prop­yl)glycine.

Mentions: 2-(2′-Carb­oxy­cyclo­prop­yl)glycines CCG-I, CCG-III and CCG-IV (Fig. 1 ▸) are naturally occuring conformationally restricted analogs of glutamate isolated from Aesculus parviflora, Blighia sapida (Fowden, et al., 1969 ▸), Ephedra foeminea (Caveney & Starratt, 1994 ▸), and Ephedra altissima (Starratt & Caveney, 1995 ▸). While not naturally occurring, both enanti­omers of CCG-II (Fig. 1 ▸) have been prepared in the laboratory (Shimamoto, et al., 1991 ▸) and all of the diastereomeric CCGs are useful tools for investigating the mechanism of glutamate function. The crystal structure of the title hydrate, (±)-CCG-III·H2O, is now reported.


Crystal structure of cis-2-(2-carb-oxy-cyclo-prop-yl)glycine (CCG-III) monohydrate.

Lindeman S, Wallock NJ, Donaldson WA - Acta Crystallogr E Crystallogr Commun (2015)

Structures of the diastereomers of 2-(2′-carb­oxy­cyclo­prop­yl)glycine.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518997&req=5

fig1: Structures of the diastereomers of 2-(2′-carb­oxy­cyclo­prop­yl)glycine.
Mentions: 2-(2′-Carb­oxy­cyclo­prop­yl)glycines CCG-I, CCG-III and CCG-IV (Fig. 1 ▸) are naturally occuring conformationally restricted analogs of glutamate isolated from Aesculus parviflora, Blighia sapida (Fowden, et al., 1969 ▸), Ephedra foeminea (Caveney & Starratt, 1994 ▸), and Ephedra altissima (Starratt & Caveney, 1995 ▸). While not naturally occurring, both enanti­omers of CCG-II (Fig. 1 ▸) have been prepared in the laboratory (Shimamoto, et al., 1991 ▸) and all of the diastereomeric CCGs are useful tools for investigating the mechanism of glutamate function. The crystal structure of the title hydrate, (±)-CCG-III·H2O, is now reported.

Bottom Line: Each mol-ecule exists as a zwitterion, with proton transfer from the amino acid carb-oxy-lic 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 inter-est 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.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, Marquette University, PO Box 1881, Milwaukee, WI 53201-1881, USA.

ABSTRACT
The title compound, C6H9NO4·H2O [systematic name: (αR,1R,2S)-rel-α-amino-2-carb-oxy-cyclo-propane-acetic acid monohydrate], crystallizes with two organic mol-ecules and two water mol-ecules in the asymmetric unit. The space group is P21 and the organic mol-ecules are enanti-omers, thus this is an example of a 'false conglomerate' with two mol-ecules of opposite handedness in the asymmetric unit (r.m.s. overlay fit = 0.056 Å for one mol-ecule and its inverted partner). Each mol-ecule exists as a zwitterion, with proton transfer from the amino acid carb-oxy-lic 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 inter-est 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.

No MeSH data available.


Related in: MedlinePlus