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Sci Adv. 2017 Apr 26;3(4):e1602847. doi: 10.1126/sciadv.1602847. eCollection 2017 Apr.

Mechanism and color modulation of fungal bioluminescence.

Author information

1
Institute of Bioorganic Chemistry, Russian Academy of Sciences, Miklukho-Maklaya 16/10, Moscow 117997, Russia.
2
Pirogov Russian National Research Medical University, Ostrovitianov 1, Moscow 117997, Russia.
3
Institute of Biophysics Siberian Branch of Russian Academy of Sciences (SB RAS), Federal Research Center "Krasnoyarsk Science Center SB RAS," Akademgorodok, Krasnoyarsk 660036, Russia.
4
Departamento de Análises Clínicas e Toxicológicas, Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, 05508-900, Brazil.
5
Graduate School of Bioagricultural Sciences, Nagoya University, Nagoya 464-8601, Japan.
6
Departamento de Bioquímica, Instituto de Química, Universidade de São Paulo, São Paulo, 05508-000, Brazil.
7
Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, São Paulo, 05508-000, Brazil.
8
Departamento de Oceanografia Física, Química e Geológica, Instituto Oceanográfico, Universidade de São Paulo, 05508-120, Brazil.
9
Department of Environmental Biology, Chubu University, Kasugai 487-8501, Japan.

Abstract

Bioluminescent fungi are spread throughout the globe, but details on their mechanism of light emission are still scarce. Usually, the process involves three key components: an oxidizable luciferin substrate, a luciferase enzyme, and a light emitter, typically oxidized luciferin, and called oxyluciferin. We report the structure of fungal oxyluciferin, investigate the mechanism of fungal bioluminescence, and describe the use of simple synthetic α-pyrones as luciferins to produce multicolor enzymatic chemiluminescence. A high-energy endoperoxide is proposed as an intermediate of the oxidation of the native luciferin to the oxyluciferin, which is a pyruvic acid adduct of caffeic acid. Luciferase promiscuity allows the use of simple α-pyrones as chemiluminescent substrates.

KEYWORDS:

CIEEL; Neonothopanus; alpha-pyrone; chemiluminescence; endoperoxide; enzyme promiscuity; hispidin; luciferase; luciferin; photochemistry

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