1,4-dihydroxy-6-naphthoate biosynthesis I

Goble AM, Toro R, Li X, Ornelas A, Fan H, Eswaramoorthy S, Patskovsky Y, Hillerich B, Seidel R, Sali A, Shoichet BK, Almo SC, Swaminathan S, Tanner ME, Raushel FM. Deamination of 6-aminodeoxyfutalosine in menaquinone biosynthesis by distantly related enzymes. Biochemistry. 2013 Sep 17;52(37):6525–36. PMID: 23972005; PMCID: PMC3813303.; Li X, Apel D, Gaynor EC, Tanner ME. 5'-Methylthioadenosine Nucleosidase Is Implicated in Playing a Key Role in a Modified Futalosine Pathway for Menaquinone Biosynthesis in Campylobacter jejuni. Journal of Biological Chemistry. 2011 Jun;286(22):19392–8. doi: 10.1074/jbc.m111.229781.; HIRATSUKA T, ITOH N, SETO H, DAIRI T. Enzymatic Properties of Futalosine Hydrolase, an Enzyme Essential to a Newly Identified Menaquinone Biosynthetic Pathway. Bioscience, Biotechnology, and Biochemistry. 2009 May 23;73(5):1137–41. doi: 10.1271/bbb.80906.; Hiratsuka T, Furihata K, Ishikawa J, Yamashita H, Itoh N, Seto H, Dairi T. An alternative menaquinone biosynthetic pathway operating in microorganisms. Science. 2008 Sep 19;321(5896):1670–3. doi: 10.1126/science.1160446. PMID: 18801996.

Metabolites



Enzyme

EC Number name full name note
1.21.98.1 cyclic dehypoxanthinyl futalosine synthase dehypoxanthine futalosine:S-adenosyl-L-methionine oxidoreductase (cyclizing)
2.5.1.120 aminodeoxyfutalosine synthase S-adenosyl-L-methionine:3-[(1-carboxyvinyl)-oxy]benzoate adenosyltransferase (bicarbonate-hydrolysing, 6-amino-6-deoxyfutalosine-forming)
3.2.2.26 futalosine hydrolase futalosine ribohydrolase
3.5.4.40 aminodeoxyfutalosine deaminase 6-amino-6-deoxyfutalosine deaminase
4.1.99.29 5,8-dihydroxy-2-naphthoate synthase cyclic dehypoxanthine futalosine lyase (dihydroxyacetone-forming)
4.2.1.151 chorismate dehydratase chorismate hydro-lyase (3-[(1-carboxyvinyl)oxy]benzoate-forming)


Proteins

Protein ID name full name
A6Q234 MQNX_NITSB Aminodeoxyfutalosine deaminase
Q5SK48 mqnE Aminodeoxyfutalosine synthase
Q5SKT7 mqnB Futalosine hydrolase
Q9KXN1 mqnD 1,4-dihydroxy-6-naphtoate synthase
Q9L0T8 mqnA Chorismate dehydratase
Q9XAP2 mqnC Cyclic dehypoxanthine futalosine synthase