Molecular recognition of ω-amino acids by thiazolobenzocrown receptors: A GABA-selective ionophore

Young Rae Yi; Ki Soo Kim; Aasif Helal; Hong Seok Kim

doi:10.1080/10610278.2012.726731

Molecular recognition of ω-amino acids by thiazolobenzocrown receptors: A GABA-selective ionophore

Young Rae Yi
, Ki Soo Kim
, Aasif Helal
, Hong Seok Kim^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

4 Scopus citations

Abstract

Three new thiazolobenzocrown (TBC) ethers conjugated with picolinic acid, benzoic acid and pyridylmethyl were synthesised and their binding properties towards amino acids were assessed by ¹H NMR titration and isothermal titration calorimety (ITC). The TBC-picolinic acid conjugate (4) showed a pronounced selectivity towards GABA by the ¹H NMR titration, and the association constant for GABA had the largest value determined by ITC. The association constant of 4 for GABA was about 19 times higher than that of glycine.

Original language	English
Pages (from-to)	16-23
Number of pages	8
Journal	Supramolecular Chemistry
Volume	25
Issue number	1
DOIs	https://doi.org/10.1080/10610278.2012.726731
State	Published - 1 Jan 2013
Externally published	Yes

Bibliographical note

Funding Information:
This study was supported by the Korea Research Foundation grant (KRF-2001-C060400-DP0332) and the NRF grant funded by the MEST in Korea (NRF-2010-0010070). The Research Institute of Industrial Technology at the Kyungpook National University also supported A.H.

Keywords

GABA
amino acid
picolinic acid
selective recognition
thiazolobenzocrown ether

ASJC Scopus subject areas

General Chemistry

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10.1080/10610278.2012.726731

Cite this

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abstract = "Three new thiazolobenzocrown (TBC) ethers conjugated with picolinic acid, benzoic acid and pyridylmethyl were synthesised and their binding properties towards amino acids were assessed by 1H NMR titration and isothermal titration calorimety (ITC). The TBC-picolinic acid conjugate (4) showed a pronounced selectivity towards GABA by the 1H NMR titration, and the association constant for GABA had the largest value determined by ITC. The association constant of 4 for GABA was about 19 times higher than that of glycine.",

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note = "Funding Information: This study was supported by the Korea Research Foundation grant (KRF-2001-C060400-DP0332) and the NRF grant funded by the MEST in Korea (NRF-2010-0010070). The Research Institute of Industrial Technology at the Kyungpook National University also supported A.H.",

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doi = "10.1080/10610278.2012.726731",

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T2 - A GABA-selective ionophore

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AU - Kim, Ki Soo

AU - Helal, Aasif

AU - Kim, Hong Seok

N1 - Funding Information: This study was supported by the Korea Research Foundation grant (KRF-2001-C060400-DP0332) and the NRF grant funded by the MEST in Korea (NRF-2010-0010070). The Research Institute of Industrial Technology at the Kyungpook National University also supported A.H.

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N2 - Three new thiazolobenzocrown (TBC) ethers conjugated with picolinic acid, benzoic acid and pyridylmethyl were synthesised and their binding properties towards amino acids were assessed by 1H NMR titration and isothermal titration calorimety (ITC). The TBC-picolinic acid conjugate (4) showed a pronounced selectivity towards GABA by the 1H NMR titration, and the association constant for GABA had the largest value determined by ITC. The association constant of 4 for GABA was about 19 times higher than that of glycine.

AB - Three new thiazolobenzocrown (TBC) ethers conjugated with picolinic acid, benzoic acid and pyridylmethyl were synthesised and their binding properties towards amino acids were assessed by 1H NMR titration and isothermal titration calorimety (ITC). The TBC-picolinic acid conjugate (4) showed a pronounced selectivity towards GABA by the 1H NMR titration, and the association constant for GABA had the largest value determined by ITC. The association constant of 4 for GABA was about 19 times higher than that of glycine.

KW - GABA

KW - amino acid

KW - picolinic acid

KW - selective recognition

KW - thiazolobenzocrown ether

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DO - 10.1080/10610278.2012.726731

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IS - 1

ER -

Molecular recognition of ω-amino acids by thiazolobenzocrown receptors: A GABA-selective ionophore

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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