Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist

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Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist. / Brehm, Lotte; Frydenvang, Karla; Krogsgaard-Larsen, Povl; Liljefors, Tommy.

In: Structural Chemistry, Vol. 9, No. 2, 1998, p. 149-155.

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

Harvard

Brehm, L, Frydenvang, K, Krogsgaard-Larsen, P & Liljefors, T 1998, 'Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist', Structural Chemistry, vol. 9, no. 2, pp. 149-155. https://doi.org/10.1023/A:1022468005689

APA

Brehm, L., Frydenvang, K., Krogsgaard-Larsen, P., & Liljefors, T. (1998). Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist. Structural Chemistry, 9(2), 149-155. https://doi.org/10.1023/A:1022468005689

Vancouver

Brehm L, Frydenvang K, Krogsgaard-Larsen P, Liljefors T. Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist. Structural Chemistry. 1998;9(2):149-155. https://doi.org/10.1023/A:1022468005689

Author

Brehm, Lotte ; Frydenvang, Karla ; Krogsgaard-Larsen, Povl ; Liljefors, Tommy. / Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist. In: Structural Chemistry. 1998 ; Vol. 9, No. 2. pp. 149-155.

Bibtex

@article{3f6e4e59e9b5402cb7a0cb4ba83a987f,
title = "Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist",
abstract = "Ibotenic acid, a constituent of Amanita muscaria, is a potent NMDA receptor agonist. The structure of the ibotenic acid zwitterion monohydrate in the crystalline state has been determined by X-ray crystallography. The crystal structure has two ibotenic acid monohydrate formula units in the asymmetric unit and features an extensive hydrogen bond network. The ibotenic acid zwitterions in the crystalline state are compared to the in vacuo structure calculated by quantum chemical ab initio calculations at the HF/6-31+G* level and the effects of the hydrogen bond network on the structures in the solid state are discussed. The calculated potential energy curve with respect to side-chain orientation displays a single energy minimum. The conformations corresponding to the solid-state conformations are calculated to be ca. 2 kcal/mol higher in energy than the minimum-energy conformation in vacuo.",
keywords = "Ab initio calculations, Conformational energy, Ibotenic acid, Molecular flexibility, X-ray structure",
author = "Lotte Brehm and Karla Frydenvang and Povl Krogsgaard-Larsen and Tommy Liljefors",
note = "Funding Information: This work was supported by grants from the Danish State Biotechnology Programme 1991-1995, the Alfred Benzon Foundation, the Lundbeck Foundation, the Danish Medical Research Council, and the Danish Natural Science Research Council. The assistance of Flemming Hansen with the X-ray data collection is gratefully acknowledged, as is the secretarial assistance of Anne-Mette Nielsen.",
year = "1998",
doi = "10.1023/A:1022468005689",
language = "English",
volume = "9",
pages = "149--155",
journal = "Structural Chemistry",
issn = "1040-0400",
publisher = "Springer",
number = "2",

}

RIS

TY - JOUR

T1 - Crystal Structure and Quantum Chemical Ab Initio Calculations of Ibotenic Acid, an Excitatory Amino Acid Receptor Agonist

AU - Brehm, Lotte

AU - Frydenvang, Karla

AU - Krogsgaard-Larsen, Povl

AU - Liljefors, Tommy

N1 - Funding Information: This work was supported by grants from the Danish State Biotechnology Programme 1991-1995, the Alfred Benzon Foundation, the Lundbeck Foundation, the Danish Medical Research Council, and the Danish Natural Science Research Council. The assistance of Flemming Hansen with the X-ray data collection is gratefully acknowledged, as is the secretarial assistance of Anne-Mette Nielsen.

PY - 1998

Y1 - 1998

N2 - Ibotenic acid, a constituent of Amanita muscaria, is a potent NMDA receptor agonist. The structure of the ibotenic acid zwitterion monohydrate in the crystalline state has been determined by X-ray crystallography. The crystal structure has two ibotenic acid monohydrate formula units in the asymmetric unit and features an extensive hydrogen bond network. The ibotenic acid zwitterions in the crystalline state are compared to the in vacuo structure calculated by quantum chemical ab initio calculations at the HF/6-31+G* level and the effects of the hydrogen bond network on the structures in the solid state are discussed. The calculated potential energy curve with respect to side-chain orientation displays a single energy minimum. The conformations corresponding to the solid-state conformations are calculated to be ca. 2 kcal/mol higher in energy than the minimum-energy conformation in vacuo.

AB - Ibotenic acid, a constituent of Amanita muscaria, is a potent NMDA receptor agonist. The structure of the ibotenic acid zwitterion monohydrate in the crystalline state has been determined by X-ray crystallography. The crystal structure has two ibotenic acid monohydrate formula units in the asymmetric unit and features an extensive hydrogen bond network. The ibotenic acid zwitterions in the crystalline state are compared to the in vacuo structure calculated by quantum chemical ab initio calculations at the HF/6-31+G* level and the effects of the hydrogen bond network on the structures in the solid state are discussed. The calculated potential energy curve with respect to side-chain orientation displays a single energy minimum. The conformations corresponding to the solid-state conformations are calculated to be ca. 2 kcal/mol higher in energy than the minimum-energy conformation in vacuo.

KW - Ab initio calculations

KW - Conformational energy

KW - Ibotenic acid

KW - Molecular flexibility

KW - X-ray structure

UR - http://www.scopus.com/inward/record.url?scp=0344640023&partnerID=8YFLogxK

U2 - 10.1023/A:1022468005689

DO - 10.1023/A:1022468005689

M3 - Journal article

AN - SCOPUS:0344640023

VL - 9

SP - 149

EP - 155

JO - Structural Chemistry

JF - Structural Chemistry

SN - 1040-0400

IS - 2

ER -

ID: 382747081