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

Author:
Hisamatsu, Yosuke, Fukiage, Takehiro, Honma, Kojiro, Balia, Andrii G., Umezawa, Naoki, Kato, Nobuki, Higuchi, Tsunehiko
Source:
Organic letters 2019 v.21 no.5 pp. 1258-1262
ISSN:
1523-7052
Subject:
chemical reactions, chemical structure, chemiluminescence, hydrogen bonding, organic compounds, pH
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 pKₐ value. This compound exhibits a superior chemiluminescence response to AMPD in the physiologically relevant pH range.
Agid:
6323509