Theoretical research on structures of γ-aminobutyric acid and glutamic acid in aqueous conditions

Kei Odai, Tohru Sugimoto, Minoru Kubo, Etsuro Ito

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Even though glutamic acid contains only one more carboxyl group than 7-aminobutyric acid (GABA), these neurotransmitters are recognized by their own specific receptors. To understand the ligand-recognition mechanism of the receptors, we must determine the geometric and electronic structures of GABA and glutamic acid in aqueous conditions using the ab initio calculation. The results of the present study showed that the stable structure of GABA was the extended form, and it attracted both cations and anions. Glutamic acid only attracted cations and was stabilized in four forms in aqueous conditions: Type 1 (an extended form), Type 2 (a rounded form), and Types 3 and 4 (twisted forms of Type 1). The former two types had low energy and the energy barrier between them was estimated to be small. These results showed that most free glutamic acid is present as Type 1, Type 2, and transient forms. The present results therefore suggest that the flexibility of the geometric structures of ligands should be taken into account when we attempt to elucidate the mechanism of recognition between ligands and receptors, in addition to the physicochemical characteristics of ligands and receptors.

Original languageEnglish
Pages (from-to)335-342
Number of pages8
JournalJournal of Biochemistry
Volume133
Issue number3
DOIs
Publication statusPublished - 2003 Mar 1
Externally publishedYes

Fingerprint

Aminobutyrates
Glutamic Acid
Ligands
Research
Cations
Energy barriers
Electronic structure
Anions
Neurotransmitter Agents

Keywords

  • GABA
  • Geometric structure
  • Glutamic acid
  • Molecular orbital method
  • Solvent effect

ASJC Scopus subject areas

  • Biochemistry

Cite this

Theoretical research on structures of γ-aminobutyric acid and glutamic acid in aqueous conditions. / Odai, Kei; Sugimoto, Tohru; Kubo, Minoru; Ito, Etsuro.

In: Journal of Biochemistry, Vol. 133, No. 3, 01.03.2003, p. 335-342.

Research output: Contribution to journalArticle

Odai, Kei ; Sugimoto, Tohru ; Kubo, Minoru ; Ito, Etsuro. / Theoretical research on structures of γ-aminobutyric acid and glutamic acid in aqueous conditions. In: Journal of Biochemistry. 2003 ; Vol. 133, No. 3. pp. 335-342.
@article{dfd8d4822c1a4b269e3f474a78fee4d9,
title = "Theoretical research on structures of γ-aminobutyric acid and glutamic acid in aqueous conditions",
abstract = "Even though glutamic acid contains only one more carboxyl group than 7-aminobutyric acid (GABA), these neurotransmitters are recognized by their own specific receptors. To understand the ligand-recognition mechanism of the receptors, we must determine the geometric and electronic structures of GABA and glutamic acid in aqueous conditions using the ab initio calculation. The results of the present study showed that the stable structure of GABA was the extended form, and it attracted both cations and anions. Glutamic acid only attracted cations and was stabilized in four forms in aqueous conditions: Type 1 (an extended form), Type 2 (a rounded form), and Types 3 and 4 (twisted forms of Type 1). The former two types had low energy and the energy barrier between them was estimated to be small. These results showed that most free glutamic acid is present as Type 1, Type 2, and transient forms. The present results therefore suggest that the flexibility of the geometric structures of ligands should be taken into account when we attempt to elucidate the mechanism of recognition between ligands and receptors, in addition to the physicochemical characteristics of ligands and receptors.",
keywords = "GABA, Geometric structure, Glutamic acid, Molecular orbital method, Solvent effect",
author = "Kei Odai and Tohru Sugimoto and Minoru Kubo and Etsuro Ito",
year = "2003",
month = "3",
day = "1",
doi = "10.1093/jb/mvg045",
language = "English",
volume = "133",
pages = "335--342",
journal = "Journal of Biochemistry",
issn = "0021-924X",
publisher = "Oxford University Press",
number = "3",

}

TY - JOUR

T1 - Theoretical research on structures of γ-aminobutyric acid and glutamic acid in aqueous conditions

AU - Odai, Kei

AU - Sugimoto, Tohru

AU - Kubo, Minoru

AU - Ito, Etsuro

PY - 2003/3/1

Y1 - 2003/3/1

N2 - Even though glutamic acid contains only one more carboxyl group than 7-aminobutyric acid (GABA), these neurotransmitters are recognized by their own specific receptors. To understand the ligand-recognition mechanism of the receptors, we must determine the geometric and electronic structures of GABA and glutamic acid in aqueous conditions using the ab initio calculation. The results of the present study showed that the stable structure of GABA was the extended form, and it attracted both cations and anions. Glutamic acid only attracted cations and was stabilized in four forms in aqueous conditions: Type 1 (an extended form), Type 2 (a rounded form), and Types 3 and 4 (twisted forms of Type 1). The former two types had low energy and the energy barrier between them was estimated to be small. These results showed that most free glutamic acid is present as Type 1, Type 2, and transient forms. The present results therefore suggest that the flexibility of the geometric structures of ligands should be taken into account when we attempt to elucidate the mechanism of recognition between ligands and receptors, in addition to the physicochemical characteristics of ligands and receptors.

AB - Even though glutamic acid contains only one more carboxyl group than 7-aminobutyric acid (GABA), these neurotransmitters are recognized by their own specific receptors. To understand the ligand-recognition mechanism of the receptors, we must determine the geometric and electronic structures of GABA and glutamic acid in aqueous conditions using the ab initio calculation. The results of the present study showed that the stable structure of GABA was the extended form, and it attracted both cations and anions. Glutamic acid only attracted cations and was stabilized in four forms in aqueous conditions: Type 1 (an extended form), Type 2 (a rounded form), and Types 3 and 4 (twisted forms of Type 1). The former two types had low energy and the energy barrier between them was estimated to be small. These results showed that most free glutamic acid is present as Type 1, Type 2, and transient forms. The present results therefore suggest that the flexibility of the geometric structures of ligands should be taken into account when we attempt to elucidate the mechanism of recognition between ligands and receptors, in addition to the physicochemical characteristics of ligands and receptors.

KW - GABA

KW - Geometric structure

KW - Glutamic acid

KW - Molecular orbital method

KW - Solvent effect

UR - http://www.scopus.com/inward/record.url?scp=0037367561&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037367561&partnerID=8YFLogxK

U2 - 10.1093/jb/mvg045

DO - 10.1093/jb/mvg045

M3 - Article

C2 - 12761169

AN - SCOPUS:0037367561

VL - 133

SP - 335

EP - 342

JO - Journal of Biochemistry

JF - Journal of Biochemistry

SN - 0021-924X

IS - 3

ER -