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Issue 18, 2015
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Convenient synthesis of deazaflavin cofactor FO and its activity in F420-dependent NADP reductase

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Abstract

F420 and FO are phenolic 5-deazaflavin cofactors that complement nicotinamide and flavin redox coenzymes in biochemical oxidoreductases and photocatalytic systems. Specifically, these 5-deazaflavins lack the single electron reactivity with O2 of riboflavin-derived coenzymes (FMN and FAD), and, in general, have a more negative redox potential than NAD(P)+. For example, F420-dependent NADP+ oxidoreductase (Fno) is critical to the conversion of CO2 to CH4 by methanogenic archaea, while FO functions as a light-harvesting agent in DNA repair. The preparation of these cofactors is an obstacle to their use in biochemical studies and biotechnology. Here, a convenient synthesis of FO was achieved by improving the redox stability of synthetic intermediates containing a polar, electron-rich aminophenol fragment. Improved yields and simplified purification techniques for FO are described. Additionally, Fno activity was restored with FO in the absence of F420. Investigating the FO-dependent NADP+/NADPH redox process by stopped-flow spectrophotometry, steady state kinetics were defined as having a Km of 4.00 ± 0.39 μM and a kcat of 5.27 ± 0.14 s−1. The preparation of FO should enable future biochemical studies and novel uses of F420 mimics.

Graphical abstract: Convenient synthesis of deazaflavin cofactor FO and its activity in F420-dependent NADP reductase

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Publication details

The article was received on 23 Feb 2015, accepted on 26 Mar 2015 and first published on 26 Mar 2015


Article type: Communication
DOI: 10.1039/C5OB00365B
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2015,13, 5082-5085
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    Convenient synthesis of deazaflavin cofactor FO and its activity in F420-dependent NADP reductase

    M. S. Hossain, C. Q. Le, E. Joseph, T. Q. Nguyen, K. Johnson-Winters and F. W. Foss, Org. Biomol. Chem., 2015, 13, 5082
    DOI: 10.1039/C5OB00365B

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