Selective anion sensing by chiral macrocyclic receptors with multiple hydrogen-bonding sites

Tadashi Ema; Keiichi Okuda; Sagiri Watanabe; Takayuki Yamasaki; Tsuyoshi Minami; Nina A. Esipenko; Pavel Anzenbacher

doi:10.1021/ol403643d

Selective anion sensing by chiral macrocyclic receptors with multiple hydrogen-bonding sites

Tadashi Ema, Keiichi Okuda, Sagiri Watanabe, Takayuki Yamasaki, Tsuyoshi Minami, Nina A. Esipenko, Pavel Anzenbacher

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

48 Citations (Scopus)

Abstract

Chiral macrocycles featuring sulfonamide and/or amide groups as anion-binding sites were synthesized. X-ray crystal structures and DFT calculations have shown that they adopt different conformations that may lead to unique binding behavior. Indeed, various anions could be sensed by their colorimetric and/or fluorescence signal output. The chiral macrocycles showed chiral recognition for chiral anions. Furthermore, a multisensor array with two or four chiral receptors discriminated seven phosphate anions (AMP, ADP, ATP, CMP, GMP, Pi, and PPi) with 100% classification accuracy.

Original language	English
Pages (from-to)	1302-1305
Number of pages	4
Journal	Organic Letters
Volume	16
Issue number	5
DOIs	https://doi.org/10.1021/ol403643d
Publication status	Published - Mar 7 2014

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol403643d

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abstract = "Chiral macrocycles featuring sulfonamide and/or amide groups as anion-binding sites were synthesized. X-ray crystal structures and DFT calculations have shown that they adopt different conformations that may lead to unique binding behavior. Indeed, various anions could be sensed by their colorimetric and/or fluorescence signal output. The chiral macrocycles showed chiral recognition for chiral anions. Furthermore, a multisensor array with two or four chiral receptors discriminated seven phosphate anions (AMP, ADP, ATP, CMP, GMP, Pi, and PPi) with 100% classification accuracy.",

author = "Tadashi Ema and Keiichi Okuda and Sagiri Watanabe and Takayuki Yamasaki and Tsuyoshi Minami and Esipenko, {Nina A.} and Pavel Anzenbacher",

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T1 - Selective anion sensing by chiral macrocyclic receptors with multiple hydrogen-bonding sites

AU - Ema, Tadashi

AU - Okuda, Keiichi

AU - Watanabe, Sagiri

AU - Yamasaki, Takayuki

AU - Minami, Tsuyoshi

AU - Esipenko, Nina A.

AU - Anzenbacher, Pavel

PY - 2014/3/7

Y1 - 2014/3/7

N2 - Chiral macrocycles featuring sulfonamide and/or amide groups as anion-binding sites were synthesized. X-ray crystal structures and DFT calculations have shown that they adopt different conformations that may lead to unique binding behavior. Indeed, various anions could be sensed by their colorimetric and/or fluorescence signal output. The chiral macrocycles showed chiral recognition for chiral anions. Furthermore, a multisensor array with two or four chiral receptors discriminated seven phosphate anions (AMP, ADP, ATP, CMP, GMP, Pi, and PPi) with 100% classification accuracy.

AB - Chiral macrocycles featuring sulfonamide and/or amide groups as anion-binding sites were synthesized. X-ray crystal structures and DFT calculations have shown that they adopt different conformations that may lead to unique binding behavior. Indeed, various anions could be sensed by their colorimetric and/or fluorescence signal output. The chiral macrocycles showed chiral recognition for chiral anions. Furthermore, a multisensor array with two or four chiral receptors discriminated seven phosphate anions (AMP, ADP, ATP, CMP, GMP, Pi, and PPi) with 100% classification accuracy.

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Selective anion sensing by chiral macrocyclic receptors with multiple hydrogen-bonding sites

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