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 Nov 24

Fingerprint

Firefly Luciferin
Fireflies
Bioluminescence
Cyclization
Luminescence
Glutamic Acid
Switches
aminoacylase I

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization. / Ioka, Shuji; Saitoh, Tsuyoshi; Maki, Shojiro A.; Imoto, Masaya; Nishiyama, Shigeru.

In: Tetrahedron, Vol. 72, No. 47, 24.11.2016, p. 7505-7508.

Research output: Contribution to journalArticle

Ioka, Shuji ; Saitoh, Tsuyoshi ; Maki, Shojiro A. ; Imoto, Masaya ; Nishiyama, Shigeru. / Development of a luminescence-controllable firefly luciferin analogue using selective enzymatic cyclization. In: Tetrahedron. 2016 ; Vol. 72, No. 47. pp. 7505-7508.
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