Gram-scale synthesis of luciferins derived from coelenterazine and original insights into their bioluminescence properties

Eloi P Coutant; Sophie Goyard; Vincent Hervin; Glwadys Gagnot; Racha Baatallah; Yves Jacob; Thierry Rose; Yves L Janin

doi:10.1039/c9ob00459a

Gram-scale synthesis of luciferins derived from coelenterazine and original insights into their bioluminescence properties

Org Biomol Chem. 2019 Apr 10;17(15):3709-3713. doi: 10.1039/c9ob00459a.

Authors

Eloi P Coutant¹, Sophie Goyard, Vincent Hervin, Glwadys Gagnot, Racha Baatallah, Yves Jacob, Thierry Rose, Yves L Janin

Affiliation

¹ Unité de Chimie et Biocatalyse, Institut Pasteur, UMR 3523, CNRS, 28 rue du Dr Roux, 75724 Paris cedex 15, France. yves.janin@pasteur.fr.

PMID: 30882838
DOI: 10.1039/c9ob00459a

Abstract

An original gram-scale synthesis of O-acetylated forms of coelenterazine, furimazine or hydroxy-bearing analogues of luciferins is described. The comparison over two hours of their bioluminescence, using the nanoKAZ/NanoLuc luciferase, provides remarkable insights useful for the selection of a substrate adapted for a given application.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Acetylation
Animals
Fireflies
Firefly Luciferin / analogs & derivatives
Firefly Luciferin / chemical synthesis*
Firefly Luciferin / chemistry
Imidazoles / chemical synthesis*
Imidazoles / chemistry
Luciferases, Firefly / metabolism
Luminescent Measurements
Molecular Structure
Pyrazines / chemical synthesis*
Pyrazines / chemistry

Substances

Imidazoles
Pyrazines
coelenterazine
Firefly Luciferin
Luciferases, Firefly