Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization

Shuji Ioka, Tsuyoshi Saitoh, Shojiro A. Maki, Masaya Imoto, Shigeru Nishiyama

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

In this study, a new firefly luciferin analog that can switch firefly bioluminescence (BL) activity from ‘off’ to ‘on’ state was designed and synthesized. BL inactive N-Ac-γ-glutamate luciferin 3 contains an acyclic precursor of the thiazoline moiety. Enzymatic treatment of 3 with aminoacylase resulted in a smooth removal of the acyl protecting group and concomitant cyclization to provide BL active carboluciferin 2.

Original languageEnglish
Pages (from-to)7505-7508
Number of pages4
JournalTetrahedron
Volume72
Issue number47
DOIs
Publication statusPublished - 2016 Jan 1

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Keywords

  • Bioluminescence
  • Enzyme detection
  • Firefly luciferase
  • Firefly luciferin derivative
  • Organic synthesis

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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