Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore

Yosuke Hisamatsu; Takehiro Fukiage; Kojiro Honma; Andrii G. Balia; Naoki Umezawa; Nobuki Kato; Tsunehiko Higuchi

doi:10.1021/acs.orglett.8b03913

Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore

Yosuke Hisamatsu, Takehiro Fukiage, Kojiro Honma, Andrii G. Balia, Naoki Umezawa, Nobuki Kato, Tsunehiko Higuchi

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

Abstract

A pioneering chemiluminescent molecule reported by Schaap and co-workers, 3-(2′-spiroadamantane)-4-methoxy-4-(3″-hydroxy)phenyl-1,2-dioxetane (AMPD), does not require enzymatic activation but is unsuitable for use under physiological conditions. To overcome this limitation, we have developed a new AMPD derivative that contains an acetamido group at the ortho position of the hydroxy group as an intramolecular hydrogen-bonding site in order to lower the pK _a value. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range.

Original language	English
Pages (from-to)	1258-1262
Number of pages	5
Journal	Organic letters
Volume	21
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.8b03913
Publication status	Published - 2019 Mar 1
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore. / Hisamatsu, Yosuke; Fukiage, Takehiro; Honma, Kojiro; Balia, Andrii G.; Umezawa, Naoki; Kato, Nobuki; Higuchi, Tsunehiko.

In: Organic letters, Vol. 21, No. 5, 01.03.2019, p. 1258-1262.

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

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abstract = " A pioneering chemiluminescent molecule reported by Schaap and co-workers, 3-(2′-spiroadamantane)-4-methoxy-4-(3″-hydroxy)phenyl-1,2-dioxetane (AMPD), does not require enzymatic activation but is unsuitable for use under physiological conditions. To overcome this limitation, we have developed a new AMPD derivative that contains an acetamido group at the ortho position of the hydroxy group as an intramolecular hydrogen-bonding site in order to lower the pK a value. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range. ",

author = "Yosuke Hisamatsu and Takehiro Fukiage and Kojiro Honma and Balia, {Andrii G.} and Naoki Umezawa and Nobuki Kato and Tsunehiko Higuchi",

note = "Funding Information: This work was supported by JSPS KAKENHI (No. 18K06551 for Y.H. and No. 17H04000 for T.H.) Publisher Copyright: {\textcopyright} 2019 American Chemical Society.",

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AU - Umezawa, Naoki

AU - Kato, Nobuki

AU - Higuchi, Tsunehiko

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Effect of the o-Acetamido Group on pH-Dependent Light Emission of a 3-Hydroxyphenyl-Substituted Dioxetane Luminophore

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