ArticleScientific reports2016
One-pot non-enzymatic formation of firefly luciferin in a neutral buffer from p-benzoquinone and cysteine.
Article in Scientific reports, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 32 citations in OpenAlex.
- A practical, biomimetic, one-pot synthesis of firefly luciferin.Scientific reports · 2024Article
- A Comprehensive Exploration of Bioluminescence Systems, Mechanisms, and Advanced Assays for Versatile Applications.Biochemistry research international · 2024Review
- Biosensing firefly luciferin synthesis in bacteria reveals a cysteine-dependent quinone detoxification route in Coleoptera.Scientific reports · 2022Article
- Genomic and experimental data provide new insights into luciferin biosynthesis and bioluminescence evolution in fireflies.Scientific reports · 2020Article
- Efficient Synthesis of Hydroxy-Substituted 2-Aminobenzo[ACS omega · 2020Article
- Enzymatic promiscuity and the evolution of bioluminescence.The FEBS journal · 2020Review
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Authors and funding
4 authors at 2 institutions in 1 country.
Funding
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Abstract
Firefly luciferin, the substrate for the bioluminescence reaction of luminous beetles, possesses a benzothiazole ring, which is rare in nature. Here, we demonstrate a novel one-pot reaction to give firefly luciferin in a neutral buffer from p-benzoquinone and cysteine without any synthetic reagents or enzymes. The formation of firefly luciferin was low in yield in various neutral buffers, whereas it was inhibited or completely prevented in acidic or basic buffers, in organic solvents, or under a nitrogen atmosphere. Labelling analysis of the firefly luciferin using stable isotopic cysteines showed that the benzothiazole ring was formed via the decarboxylation and carbon-sulfur bond rearrangement of cysteine. These findings imply that the biosynthesis of firefly luciferin can be developed/evolved from the non-enzymatic production of firefly luciferin using common primary biosynthetic units, p-benzoquinone and cysteine.
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