Science Advances

Supplementary Materials

This PDF file includes:

  • Synthetic procedures
  • fig. S1. Determination of fluorescence quantum yield of the oxyluciferin.
  • fig. S2. Determination of the chemiluminescence and singlet quantum yields of the luciferin/luciferase reaction.
  • fig. S3. Dependence of the chemiluminescence intensity from luciferin/luciferase reaction on the concentration of luciferin (76 to 760 nM) and phosphate buffer (pH 6 to 8).
  • fig. S4. Photocathode spectral response curve provided by Berthold Detection Systems (PMT type 9107).
  • fig. S5. Dynamics of the reaction between substrate and luciferase microsomal preparation of N. nambi.
  • fig. S6. Chemiluminescence spectra of 1 (orange curve) and 3 (green curve) and the fluorescence spectrum of 4 in acetone (dotted curve).
  • fig. S7. Chemiluminescence from the reaction of 1,4-dimethylnaphthalene endoperoxide (DMNO2) with 3-hydroxyhispidin (luciferin).
  • fig. S8. Collision-induced dissociation spectrum (ESI-MS/MS) of the labeled oxyluciferin—compound 4.
  • fig. S9. Absorption (blue) and fluorescence emission (red) spectra of compounds 2, 3, and 5 to 9.
  • fig. S10. Isolation and identification of compounds in peaks 2 and 4 of the luciferin 1/luciferase reaction.
  • fig. S11. Proposed mechanisms for oxyluciferin degradation.
  • fig. S12. Synthesis of the fungal luciferin 1.
  • fig. S13. Synthesis of 3,4-dihydroxy-6-methyl-2H-pyran-2-one 13.
  • fig. S14. Synthesis of compounds 14 to 16.
  • fig. S15. Synthesis of fungal luciferin analogs 3 and 5 to 9.
  • fig. S16. Synthesis of fungal oxyluciferins 2 and 4.
  • fig. S17. NMR spectra chemical shifts of compounds 18 to 23.
  • fig. S18. NMR spectra chemical shifts of luciferin analogs 3 and 5 to 9.
  • table S1. Observed decay rate constants (kobs), the total light emitted (Q) by the reaction of luciferin/luciferase reaction, and chemiluminescence and singlet quantum yields (ΦCL and ΦS) at different pH and substrate concentrations.
  • table S2. Dependence of chemiluminescence quantum yield (ΦCL) and singlet quantum yield (ΦS) on the pH of luciferin-luciferase reaction.
  • table S3. Spectral characteristics of compounds 1 to 3 and 5 to 9.
  • table S4. Observed decay rate constant (kobs), the total of light emission (Q), photomultiplier sensitivity correction factor (fPMT), and the chemiluminescence quantum yield (ΦCL) obtained from the reaction between the crude extract of N. gardneri and compounds 1, 3, and 5 to 9.

Download PDF

Files in this Data Supplement: