Reaction: 5-amino-6-(D-ribitylamino)uracil + 3-(4-hydroxyphenyl)pyruvate + 2 S-adenosyl-L-methionine + H2O = 7,8-didemethyl-8-hydroxy-5-deazariboflavin + 2 L-methionine + 2 5'-deoxyadenosine + oxalate + NH3
For diagram of reaction, click here
Glossary: 5-amino-6-(D-ribitylamino)uracil = 5-amino-6-(1-D-ribitylamino)pyrimidine-2,4(1H,3H)-dione
Other name(s): FO synthase
Systematic name: 5-amino-6-(D-ribitylamino)uracil:4-hydroxyphenylpyruvate, 4-methylphenol transferase
Comments: Binds a 4Fe-4S cluster. The cluster is coordinated by 3 cysteines and an exchangeable AdoMet molecule. The first stage of catalysis is reduction of the 2 AdoMet to produce give 2 methionine and 2 5'-deoxyadenosin-5-yl radicals that extracts a hydrogen from each of the substrates permitting the condensation of the two [1]. The overall reaction catalysed is the transfer of the hydroxybenzyl group from 4-hydroxyphenylpyruvate (HPP) to 5-amino-6-ribitylaminopyrimidine-2,4(1H,3H)-dione to form 7,8-didemethyl-8-hydroxy-5-deazariboflavin (FO). 7,8-Didemethyl-8-hydroxy-5-deazariboflavin is the chromophore of the hydride carrier coenzyme F420 [1].
Links to other databases: BRENDA, EXPASY, KEGG, Metacyc, CAS registry number:
References:
1. Graham, D.E., Xu, H. and White, R.H. Identification of the 7,8-didemethyl-8-hydroxy-5-deazariboflavin synthase required for coenzyme F420 biosynthesis. Arch. Microbiol. 180 (2003) 455-464. [PMID: 14593448]
2. Choi, K.P., Kendrick, N. and Daniels, L. Demonstration that fbiC is required by Mycobacterium bovis BCG for coenzyme F420 and FO biosynthesis. J. Bacteriol. 184 (2002) 2420-2428. [PMID: 11948155]