Why is firefly oxyluciferin a notoriously labile substance?

Oleg V. Maltsev, Naba K. Nath, Pance Naumov, Lukas Hintermann

    Research output: Contribution to journalArticle

    Abstract

    The chemistry of firefly bioluminescence is important for numerous applications in biochemistry and analytical chemistry. The emitter of this bioluminescent system, firefly oxyluciferin, is difficult to handle. The cause of its lability was clarified while its synthesis was reinvestigated. A side product was identified and characterized by NMR spectroscopy and X-ray crystallography. The reason for the lability of oxyluciferin is now ascribed to autodimerization of the coexisting enol and keto forms in a Mannich-type reaction. Light into the darkness: Firefly oxyluciferin, the emitter of firefly bioluminescence, is notoriously difficult to handle. The cause behind its chemical lability is now ascribed to autodimerization of the coexisting enol (showing blue fluorescence in DMSO) and keto forms (contributing to the green fluorescence in water) in a Mannich reaction.

    Original languageEnglish (US)
    Pages (from-to)847-850
    Number of pages4
    JournalAngewandte Chemie - International Edition
    Volume53
    Issue number3
    DOIs
    StatePublished - Jan 14 2014

    Fingerprint

    Bioluminescence
    Fluorescence
    Biochemistry
    X ray crystallography
    Nuclear magnetic resonance spectroscopy
    Dimethyl Sulfoxide
    Chemical analysis
    Water
    oxyluciferin

    Keywords

    • bioorganic chemistry
    • heterocycles
    • luminescence
    • natural products
    • structure elucidation

    ASJC Scopus subject areas

    • Catalysis
    • Chemistry(all)

    Cite this

    Why is firefly oxyluciferin a notoriously labile substance? / Maltsev, Oleg V.; Nath, Naba K.; Naumov, Pance; Hintermann, Lukas.

    In: Angewandte Chemie - International Edition, Vol. 53, No. 3, 14.01.2014, p. 847-850.

    Research output: Contribution to journalArticle

    Maltsev, Oleg V. ; Nath, Naba K. ; Naumov, Pance ; Hintermann, Lukas. / Why is firefly oxyluciferin a notoriously labile substance?. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 3. pp. 847-850.
    @article{d51029a101434ce4a8fd8341c21446da,
    title = "Why is firefly oxyluciferin a notoriously labile substance?",
    abstract = "The chemistry of firefly bioluminescence is important for numerous applications in biochemistry and analytical chemistry. The emitter of this bioluminescent system, firefly oxyluciferin, is difficult to handle. The cause of its lability was clarified while its synthesis was reinvestigated. A side product was identified and characterized by NMR spectroscopy and X-ray crystallography. The reason for the lability of oxyluciferin is now ascribed to autodimerization of the coexisting enol and keto forms in a Mannich-type reaction. Light into the darkness: Firefly oxyluciferin, the emitter of firefly bioluminescence, is notoriously difficult to handle. The cause behind its chemical lability is now ascribed to autodimerization of the coexisting enol (showing blue fluorescence in DMSO) and keto forms (contributing to the green fluorescence in water) in a Mannich reaction.",
    keywords = "bioorganic chemistry, heterocycles, luminescence, natural products, structure elucidation",
    author = "Maltsev, {Oleg V.} and Nath, {Naba K.} and Pance Naumov and Lukas Hintermann",
    year = "2014",
    month = "1",
    day = "14",
    doi = "10.1002/anie.201307972",
    language = "English (US)",
    volume = "53",
    pages = "847--850",
    journal = "Angewandte Chemie - International Edition",
    issn = "1433-7851",
    number = "3",

    }

    TY - JOUR

    T1 - Why is firefly oxyluciferin a notoriously labile substance?

    AU - Maltsev, Oleg V.

    AU - Nath, Naba K.

    AU - Naumov, Pance

    AU - Hintermann, Lukas

    PY - 2014/1/14

    Y1 - 2014/1/14

    N2 - The chemistry of firefly bioluminescence is important for numerous applications in biochemistry and analytical chemistry. The emitter of this bioluminescent system, firefly oxyluciferin, is difficult to handle. The cause of its lability was clarified while its synthesis was reinvestigated. A side product was identified and characterized by NMR spectroscopy and X-ray crystallography. The reason for the lability of oxyluciferin is now ascribed to autodimerization of the coexisting enol and keto forms in a Mannich-type reaction. Light into the darkness: Firefly oxyluciferin, the emitter of firefly bioluminescence, is notoriously difficult to handle. The cause behind its chemical lability is now ascribed to autodimerization of the coexisting enol (showing blue fluorescence in DMSO) and keto forms (contributing to the green fluorescence in water) in a Mannich reaction.

    AB - The chemistry of firefly bioluminescence is important for numerous applications in biochemistry and analytical chemistry. The emitter of this bioluminescent system, firefly oxyluciferin, is difficult to handle. The cause of its lability was clarified while its synthesis was reinvestigated. A side product was identified and characterized by NMR spectroscopy and X-ray crystallography. The reason for the lability of oxyluciferin is now ascribed to autodimerization of the coexisting enol and keto forms in a Mannich-type reaction. Light into the darkness: Firefly oxyluciferin, the emitter of firefly bioluminescence, is notoriously difficult to handle. The cause behind its chemical lability is now ascribed to autodimerization of the coexisting enol (showing blue fluorescence in DMSO) and keto forms (contributing to the green fluorescence in water) in a Mannich reaction.

    KW - bioorganic chemistry

    KW - heterocycles

    KW - luminescence

    KW - natural products

    KW - structure elucidation

    UR - http://www.scopus.com/inward/record.url?scp=84891837896&partnerID=8YFLogxK

    UR - http://www.scopus.com/inward/citedby.url?scp=84891837896&partnerID=8YFLogxK

    U2 - 10.1002/anie.201307972

    DO - 10.1002/anie.201307972

    M3 - Article

    VL - 53

    SP - 847

    EP - 850

    JO - Angewandte Chemie - International Edition

    JF - Angewandte Chemie - International Edition

    SN - 1433-7851

    IS - 3

    ER -