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. Author manuscript; available in PMC: 2017 Jun 1.
Published in final edited form as: Curr Opin Chem Biol. 2016 Sep 14;35:80–88. doi: 10.1016/j.cbpa.2016.08.029

Figure 4. Oxidation and prenylation.

Figure 4

(a) Simplified reaction scheme for the reaction catalyzed by the thiazoline and/or oxazoline oxidase protein. During the course of the reactions, oxidized flavine mononucleotide (FMN-ox) receives either one hydride and one proton or 2 single electrons and 2 protons from the thiazoline or oxazoline, generating reduced flavine mononucleotide (FMN-red). The exact mechanism remains to be determined. The catalytic competent FMN-ox is produced by reaction with oxygen to release hydrogen peroxide. (b) Tyrosine O- and C-prenylation as examples of prenylation in cyanobactins. The hydroxyl group on tyrosine is reverse O-prenylated by LynF using DMAPP (Dimethylallyl pyrophosphate). The product can subsequently undergo non-enzymatic Claisen rearrangement to give C-prenylated tyrosine.