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 journalArticlepeer-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 languageEnglish
Pages (from-to)1258-1262
Number of pages5
JournalOrganic letters
Volume21
Issue number5
DOIs
Publication statusPublished - 2019 Mar 1
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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