Design and synthesis of a more highly selective ammonium ionophore than nonactin and its application as an ion-sensing component for an ion-selective electrode

Koji Suzuki, Dwi Siswanta, Takeshi Otsuka, Tsuyoshi Amano, Takafumi Ikeda, Hideaki Hisamoto, Ryoko Yoshihara, Shigeru Ohba

Research output: Contribution to journalArticle

39 Citations (Scopus)

Abstract

A novel ammonium ionophore, which exhibits superior NH4+ selectivity compared with that of the natural antibiotic nonactin, was successfully designed and synthesized based on a 19-membered crown compound (TD19C6) having three decalino subunits in the macrocyclic system. This bulky decalino subunit is effective for (1) increasing the structural rigidity of the cyclic compound, (2) introducing the 'block-wall effect', which prevents forming a complex with a large ion, and (3) increasing the lipophilicity of the ionophore molecule. In the ammonium ionophore design, the first factor contributes to increasing the NH4+ selectivity relative to smaller ions such as Li+, Na+, or even the closest size, K+, and the second factor increases the NH4+ selectivity over larger ions such as Rb+ and Cs+. The X-ray structural analysis proved that TD19C6 forms a size-fit complex with NH4+ in its crown ring cavity. As an application of this ionophore, an ion sensor (ion-selective electrode) was prepared, which exhibited NH4+ to K+ and Na+ selectivity of 10 and 3000 times, respectively. This electrode showed a better performance compared to the electrode based on nonactin, which is the only ammonium ionophore presently used in practical applications.

Original languageEnglish
Pages (from-to)2200-2205
Number of pages6
JournalAnalytical Chemistry
Volume72
Issue number10
DOIs
Publication statusPublished - 2000 May 15

Fingerprint

Ionophores
Ammonium Compounds
Ions
Heavy ions
Crown Compounds
Electrodes
Structural analysis
Rigidity
Ion-Selective Electrodes
nonactin
Anti-Bacterial Agents
X rays
Molecules
Sensors

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

Design and synthesis of a more highly selective ammonium ionophore than nonactin and its application as an ion-sensing component for an ion-selective electrode. / Suzuki, Koji; Siswanta, Dwi; Otsuka, Takeshi; Amano, Tsuyoshi; Ikeda, Takafumi; Hisamoto, Hideaki; Yoshihara, Ryoko; Ohba, Shigeru.

In: Analytical Chemistry, Vol. 72, No. 10, 15.05.2000, p. 2200-2205.

Research output: Contribution to journalArticle

Suzuki, Koji ; Siswanta, Dwi ; Otsuka, Takeshi ; Amano, Tsuyoshi ; Ikeda, Takafumi ; Hisamoto, Hideaki ; Yoshihara, Ryoko ; Ohba, Shigeru. / Design and synthesis of a more highly selective ammonium ionophore than nonactin and its application as an ion-sensing component for an ion-selective electrode. In: Analytical Chemistry. 2000 ; Vol. 72, No. 10. pp. 2200-2205.
@article{003112dd94c24fa3889cd9515dc62eeb,
title = "Design and synthesis of a more highly selective ammonium ionophore than nonactin and its application as an ion-sensing component for an ion-selective electrode",
abstract = "A novel ammonium ionophore, which exhibits superior NH4+ selectivity compared with that of the natural antibiotic nonactin, was successfully designed and synthesized based on a 19-membered crown compound (TD19C6) having three decalino subunits in the macrocyclic system. This bulky decalino subunit is effective for (1) increasing the structural rigidity of the cyclic compound, (2) introducing the 'block-wall effect', which prevents forming a complex with a large ion, and (3) increasing the lipophilicity of the ionophore molecule. In the ammonium ionophore design, the first factor contributes to increasing the NH4+ selectivity relative to smaller ions such as Li+, Na+, or even the closest size, K+, and the second factor increases the NH4+ selectivity over larger ions such as Rb+ and Cs+. The X-ray structural analysis proved that TD19C6 forms a size-fit complex with NH4+ in its crown ring cavity. As an application of this ionophore, an ion sensor (ion-selective electrode) was prepared, which exhibited NH4+ to K+ and Na+ selectivity of 10 and 3000 times, respectively. This electrode showed a better performance compared to the electrode based on nonactin, which is the only ammonium ionophore presently used in practical applications.",
author = "Koji Suzuki and Dwi Siswanta and Takeshi Otsuka and Tsuyoshi Amano and Takafumi Ikeda and Hideaki Hisamoto and Ryoko Yoshihara and Shigeru Ohba",
year = "2000",
month = "5",
day = "15",
doi = "10.1021/ac9911241",
language = "English",
volume = "72",
pages = "2200--2205",
journal = "Analytical Chemistry",
issn = "0003-2700",
publisher = "American Chemical Society",
number = "10",

}

TY - JOUR

T1 - Design and synthesis of a more highly selective ammonium ionophore than nonactin and its application as an ion-sensing component for an ion-selective electrode

AU - Suzuki, Koji

AU - Siswanta, Dwi

AU - Otsuka, Takeshi

AU - Amano, Tsuyoshi

AU - Ikeda, Takafumi

AU - Hisamoto, Hideaki

AU - Yoshihara, Ryoko

AU - Ohba, Shigeru

PY - 2000/5/15

Y1 - 2000/5/15

N2 - A novel ammonium ionophore, which exhibits superior NH4+ selectivity compared with that of the natural antibiotic nonactin, was successfully designed and synthesized based on a 19-membered crown compound (TD19C6) having three decalino subunits in the macrocyclic system. This bulky decalino subunit is effective for (1) increasing the structural rigidity of the cyclic compound, (2) introducing the 'block-wall effect', which prevents forming a complex with a large ion, and (3) increasing the lipophilicity of the ionophore molecule. In the ammonium ionophore design, the first factor contributes to increasing the NH4+ selectivity relative to smaller ions such as Li+, Na+, or even the closest size, K+, and the second factor increases the NH4+ selectivity over larger ions such as Rb+ and Cs+. The X-ray structural analysis proved that TD19C6 forms a size-fit complex with NH4+ in its crown ring cavity. As an application of this ionophore, an ion sensor (ion-selective electrode) was prepared, which exhibited NH4+ to K+ and Na+ selectivity of 10 and 3000 times, respectively. This electrode showed a better performance compared to the electrode based on nonactin, which is the only ammonium ionophore presently used in practical applications.

AB - A novel ammonium ionophore, which exhibits superior NH4+ selectivity compared with that of the natural antibiotic nonactin, was successfully designed and synthesized based on a 19-membered crown compound (TD19C6) having three decalino subunits in the macrocyclic system. This bulky decalino subunit is effective for (1) increasing the structural rigidity of the cyclic compound, (2) introducing the 'block-wall effect', which prevents forming a complex with a large ion, and (3) increasing the lipophilicity of the ionophore molecule. In the ammonium ionophore design, the first factor contributes to increasing the NH4+ selectivity relative to smaller ions such as Li+, Na+, or even the closest size, K+, and the second factor increases the NH4+ selectivity over larger ions such as Rb+ and Cs+. The X-ray structural analysis proved that TD19C6 forms a size-fit complex with NH4+ in its crown ring cavity. As an application of this ionophore, an ion sensor (ion-selective electrode) was prepared, which exhibited NH4+ to K+ and Na+ selectivity of 10 and 3000 times, respectively. This electrode showed a better performance compared to the electrode based on nonactin, which is the only ammonium ionophore presently used in practical applications.

UR - http://www.scopus.com/inward/record.url?scp=0034656436&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034656436&partnerID=8YFLogxK

U2 - 10.1021/ac9911241

DO - 10.1021/ac9911241

M3 - Article

AN - SCOPUS:0034656436

VL - 72

SP - 2200

EP - 2205

JO - Analytical Chemistry

JF - Analytical Chemistry

SN - 0003-2700

IS - 10

ER -