Angewandte Chemie The chemical basis of fungal bioluminescence --Manuscript Draft-- Manuscript Number: 201501779R3 Article Type: Communication Corresponding Author: Ilia V Yampolsky M.M. Shemyakin and Yu.A. Ovchinnikov Institute of bioorganic chemistry Moscow, RUSSIAN FEDERATION Corresponding Author E-Mail: ivyamp@gmail.com Other Authors: Konstantin Purtov Valentin Petushkov Mikhail Baranov Konstantin Mineev Natalja Rodionova Zinaida Kaskova Aleksandra Tsarkova Alexei Petunin Vladimir Bondar Emma Rodicheva Svetlana Medvedeva Yuichi Oba Yumiko Oba Alexander Arseniev Sergey Lukyanov Josef Gitelson Abstract: Many species of fungi naturally produce light, a phenomenon known as bioluminescence, however, the fungal substrates used in the chemical reactions that produce light have not been reported. We identified the fungal luciferin, 3- hydroxyhispidin, which is biosynthesized by oxidation of the precursor hispidin, a known fungal and plant secondary metabolite. The fungal luciferin does not share structural similarity with the other eight known luciferins. Furthermore, it was shown that 3-hydroxyhispidin leads to bioluminescence in extracts from four diverse genera of luminous fungi, suggesting a common biochemical mechanism for fungal bioluminescence. Response to Reviewers: Dear Editor, Thank you for your positive decision on our manuscript 201501779R2 "The chemical basis of fungal bioluminescence"! Reviewer3 requested the following changes: “The authors have made several relevant modifications to the manuscript, which now appears suitable for publication except for one notational inaccuracy. They state in Figure 1, and in the main text referring to Figure 1, that the luminescence data is reported in units of S/N. The method for calculating S/N was not included in earlier drafts, but is included in Supporting Information of the most recent draft. However, the provided calculation is not properly an expression of S/N, as noise (N) is a determination of statistical variability in the data (typically the standard deviation of the background). Rather, by measuring "cold extract + NADPH" in absence of the compounds, the authors have determined the background of the assay. Thus the reported data is of the compound luminescence relative to the background, or S/B, not Powered by Editorial Manager® and ProduXion Manager® from Aries Systems Corporation