Escherichia coli K-12 substr. MG1655 Compound Class: an oxidized coenzyme F420

Synonyms: an oxidized factor F420

Superclasses: a cofactor a prosthetic group a coenzyme F420

One of the distinguishing features of methanogenic bacteria is their blue-green fluorescence when irradiated with UV light. This fluorescence is due to F420, a cofactor that was identified on the basis of this feature. This compound, named for its intense absorbance at 420 nm, was originally isolated by Cheeseman et al [Cheeseman72], and later identified by Eirich et al as the N-(N-L-lactyl-γ-L-glutamyl)-L- glutamic acid phosphodiester of 7,8-didemethyl-8-hydroxy-5-deazariboflavin 5'-phosphate [Eirich78].

F420 biosynthetic pathway produces the intermediate F420-0, which contains no glutamate side chains. Glutamates are then added by several enzymes. F420 molecules isolated from different organisms differ in the number of the glutamate molecules in the side chains, as well as the nature of the bond (which could be either α or γ) [Li03, Graupner03, Choi01].

an oxidized coenzyme F<sub>420</sub> compound structure

SMILES: CC(C(=O)[R])OP([O-])(=O)OCC(O)C(O)C(O)CN3(C1(C(C(=O)NC(=O)N=1)=CC2(=CC=C(O)C=C23)))


Cheeseman72: Cheeseman P, Toms-Wood A, Wolfe RS (1972). "Isolation and properties of a fluorescent compound, factor 420 , from Methanobacterium strain M.o.H." J Bacteriol 112(1);527-31. PMID: 5079072

Choi01: Choi KP, Bair TB, Bae YM, Daniels L (2001). "Use of transposon Tn5367 mutagenesis and a nitroimidazopyran-based selection system to demonstrate a requirement for fbiA and fbiB in coenzyme F(420) biosynthesis by Mycobacterium bovis BCG." J Bacteriol 183(24);7058-66. PMID: 11717263

Eirich78: Eirich LD, Vogels GD, Wolfe RS (1978). "Proposed structure for coenzyme F420 from Methanobacterium." Biochemistry 17(22);4583-93. PMID: 728375

Graupner03: Graupner M, White RH (2003). "Methanococcus jannaschii coenzyme F420 analogs contain a terminal alpha-linked glutamate." J Bacteriol 185(15);4662-5. PMID: 12867481

Li03: Li H, Xu H, Graham DE, White RH (2003). "Glutathione synthetase homologs encode alpha-L-glutamate ligases for methanogenic coenzyme F420 and tetrahydrosarcinapterin biosyntheses." Proc Natl Acad Sci U S A 100(17);9785-90. PMID: 12909715

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Please cite the following article in publications resulting from the use of EcoCyc: Nucleic Acids Research 41:D605-12 2013
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