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

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

Eloi P. Coutant,

^a Sophie Goyard,

^b Vincent Hervin,^a Glwadys Gagnot,

^ac Racha Baatallah,^a Yves Jacob,

^d Thierry Rose

*^b and Yves L. Janin

*^a

Author affiliations

* Corresponding authors

^a Unité de Chimie et Biocatalyse, Institut Pasteur, UMR 3523, CNRS, 28 rue du Dr Roux, 75724 Paris cedex 15, France
E-mail: yves.janin@pasteur.fr

^b Center for Innovation and Technological Research, Institut Pasteur, 25 rue du Dr Roux, 75724 Paris cedex 15, France
E-mail: thierry.rose@pasteur.fr

^c Université Paris Descartes, Sorbonne Paris Cité, 12 rue de l'Ecole de Médecine, 75006 Paris, France

^d Unité de Génétique Moléculaire des Virus à ARN, Institut Pasteur, UMR 3569, CNRS, 28 rue du Dr Roux, 75724 Paris cedex 15, France

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.

This article is part of the themed collection: Synthetic methodology in OBC

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Article information

DOI: https://doi.org/10.1039/C9OB00459A
Article type: Communication
Submitted: 23 Feb 2019
Accepted: 07 Mar 2019
First published: 07 Mar 2019

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Org. Biomol. Chem., 2019,17, 3709-3713

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

E. P. Coutant, S. Goyard, V. Hervin, G. Gagnot, R. Baatallah, Y. Jacob, T. Rose and Y. L. Janin, Org. Biomol. Chem., 2019, 17, 3709 DOI: 10.1039/C9OB00459A

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Organic & Biomolecular Chemistry

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

Abstract

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

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