ArticlePloS one2013
Biosynthesis of firefly luciferin in adult lantern: decarboxylation of L-cysteine is a key step for benzothiazole ring formation in firefly luciferin synthesis.
Article in PloS one, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed, 44 citations in OpenAlex.
- Recent advances in zirconium-based catalysis and its applications in organic synthesis: a review.RSC advances · 2025Review
- Molecular basis of the explosive defence response in the bombardier beetleRoyal Society open science · 2025Article
- A practical, biomimetic, one-pot synthesis of firefly luciferin.Scientific reports · 2024Article
- Scalable Thiol Reactivity Profiling Identifies Azetidinyl Oxadiazoles as Cysteine-Targeting Electrophiles.Journal of the American Chemical Society · 2024Article
- Biosensing firefly luciferin synthesis in bacteria reveals a cysteine-dependent quinone detoxification route in Coleoptera.Scientific reports · 2022Article
- Meroterpenoids: A Comprehensive Update Insight on Structural Diversity and Biology.Biomolecules · 2021Review
- Article
- Bioluminescent Imaging Systems for Assay Developments.Analytical sciences : the international journal of the Japan Society for Analytical Chemistry · 2021Review
- Genomic and experimental data provide new insights into luciferin biosynthesis and bioluminescence evolution in fireflies.Scientific reports · 2020Article
- Seeing (and Using) the Light: Recent Developments in Bioluminescence Technology.Cell chemical biology · 2020Review
- Enzymatic promiscuity and the evolution of bioluminescence.The FEBS journal · 2020Review
- Article
- New Zealand glowworm (Arachnocampa luminosa) bioluminescence is produced by a firefly-like luciferase but an entirely new luciferin.Scientific reports · 2018Article
- In Vivo Analysis of Protein-Protein Interactions with Bioluminescence Resonance Energy Transfer (BRET): Progress and Prospects.International journal of molecular sciences · 2016Review
- One-pot non-enzymatic formation of firefly luciferin in a neutral buffer from p-benzoquinone and cysteine.Scientific reports · 2016Article
- Article
- Beyond D-luciferin: expanding the scope of bioluminescence imaging in vivo.Current opinion in chemical biology · 2014Review
Corrections and comments
- Erratum issued
Authors and funding
5 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
backgroundBioluminescence in fireflies and click beetles is produced by a luciferase-luciferin reaction. The luminescence property and protein structure of firefly luciferase have been investigated, and its cDNA has been used for various assay systems. The chemical structure of firefly luciferin was identified as the D-form in 1963 and studies on the biosynthesis of firefly luciferin began early in the 1970's. Incorporation experiments using (14)C-labeled compounds were performed, and cysteine and benzoquinone/hydroquinone were proposed to be biosynthetic component for firefly luciferin. However, there have been no clear conclusions regarding the biosynthetic components of firefly luciferin over 30 years. METHODOLOGY/PRINCIPAL
findingsIncorporation studies were performed by injecting stable isotope-labeled compounds, including L-[U-(13)C3]-cysteine, L-[1-(13)C]-cysteine, L-[3-(13)C]-cysteine, 1,4-[D6]-hydroquinone, and p-[2,3,5,6-D]-benzoquinone, into the adult lantern of the living Japanese firefly Luciola lateralis. After extracting firefly luciferin from the lantern, the incorporation of stable isotope-labeled compounds into firefly luciferin was identified by LC/ESI-TOF-MS. The positions of the stable isotope atoms in firefly luciferin were determined by the mass fragmentation of firefly luciferin.
conclusionsWe demonstrated for the first time that D- and L-firefly luciferins are biosynthesized in the lantern of the adult firefly from two L-cysteine molecules with p-benzoquinone/1,4-hydroquinone, accompanied by the decarboxylation of L-cysteine.
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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.