Comparative study of the photoprotolytic reactions of D-luciferin and oxyluciferin

Yuval Erez, Itay Presiado, Rinat Gepshtein, Luís Pinto Da Silva, Joaquim C.G. Esteves Da Silva, Dan Huppert*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

39 Scopus citations

Abstract

Optical steady-state and time-resolved spectroscopic methods were used to study the photoprotolytic reaction of oxyluciferin, the active bioluminescence chromophore of the firefly's luciferase-catalyzed reaction. We found that like d-luciferin, the substrate of the firefly bioluminescence reaction, oxyluciferin is a photoacid with pKa* value of ∼0.5, whereas the excited-state proton transfer (ESPT) rate coefficient is 2.2 × 10 10 s-1, which is somewhat slower than that of d-luciferin. The kinetic isotope effect (KIE) on the fluorescence decay of oxyluciferin is 2.5 ± 0.1, the same value as that of d-luciferin. Both chromophores undergo fluorescence quenching in solutions with a pH value below 3.

Original languageEnglish
Pages (from-to)7452-7461
Number of pages10
JournalJournal of Physical Chemistry A
Volume116
Issue number28
DOIs
StatePublished - 19 Jul 2012

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