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Chemical Compound Review:

DMK-8 2- [(2E,6E,10E,14E,18E,22E,26E)- 3,7,11,15...

Synonyms: SureCN2477602, CHEBI:48455, LMPR02030027, AC1NT9WK, 29790-47-4, ...

Tyson, K. et al., Shineberg, B. et al., Unden, G. et al., Lee, P.T. et al., Huycke, M.M. et al., et al.

Huycke, Moore, Unden, Bongaerts,

Welcome! If you are familiar with the subject of this article, you can contribute to this open access knowledge base by deleting incorrect information, restructuring or completely rewriting any text. Read more.

Disease relevance of demethylmenaquinone

Enterococcus faecalis is an intestinal commensal that produces extracellular superoxide (O(2)(*-)) through autoxidation of membrane-associated demethylmenaquinone [1].
It has been postulated that 1,4-dihydroxy-2-naphthoic acid is the naphthalenic intermediate in the biosynthesis of menaquinone (vitamin K2) in Escherichia coli to which the octaprenyl side chain is attached to from demethylmenaquinone [2].

High impact information on demethylmenaquinone

E. coli strains containing either the disruption or the point mutation in ubiE accumulated 2-octaprenyl-6-methoxy-1,4-benzoquinone and demethylmenaquinone as predominant intermediates [3].
Correlation of the function of demethylmenaquinone in bacterial electron transport with its redox potential [4].
The combined data establish that menaquinones are essential for cytochrome-c-dependent trimethylamine-N-oxide reductase (Tor) and Nrf activity, but that either menaquinone or ubiquinone, but not demethylmenaquinone, can transfer electrons to a third cytochrome-c-dependent electron transfer chain, the periplasmic nitrate reductase [5].

Chemical compound and disease context of demethylmenaquinone

The electron-transport chains of Escherichia coli are composed of many different dehydrogenases and terminal reductases (or oxidases) which are linked by quinones (ubiquinone, menaquinone and demethylmenaquinone) [6].

References

In vivo production of hydroxyl radical by Enterococcus faecalis colonizing the intestinal tract using aromatic hydroxylation. Huycke, M.M., Moore, D.R. Free Radic. Biol. Med. (2002) [Pubmed]
Biosynthesis of bacterial menaquinones: the membrane-associated 1,4-dihydroxy-2-naphthoate octaprenyltransferase of Escherichia coli. Shineberg, B., Young, I.G. Biochemistry (1976) [Pubmed]
A C-methyltransferase involved in both ubiquinone and menaquinone biosynthesis: isolation and identification of the Escherichia coli ubiE gene. Lee, P.T., Hsu, A.Y., Ha, H.T., Clarke, C.F. J. Bacteriol. (1997) [Pubmed]
Correlation of the function of demethylmenaquinone in bacterial electron transport with its redox potential. Holländer, R. FEBS Lett. (1976) [Pubmed]
Characterisation of Escherichia coli K-12 mutants defective in formate-dependent nitrite reduction: essential roles for hemN and the menFDBCE operon. Tyson, K., Metheringham, R., Griffiths, L., Cole, J. Arch. Microbiol. (1997) [Pubmed]
Alternative respiratory pathways of Escherichia coli: energetics and transcriptional regulation in response to electron acceptors. Unden, G., Bongaerts, J. Biochim. Biophys. Acta (1997) [Pubmed]

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