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

5'-Deoxyadenosine

Formula: C10H13N5O3 (251.10183480000003)

CAS ID: 4754-39-6

H+

Formula: H (1.0078246)

CAS ID: 12408-02-5

H2O

Formula: H2O (18.0105642)

CAS ID: 7732-18-5

HCO3-

Formula: HCO3 (60.9925696)

CAS ID: 71-52-3

Hypoxanthine

Formula: C5H4N4O (136.03850939999998)

CAS ID: 68-94-0

3-[(1-carboxylatovinyl)oxy]benzoate(2-)

Formula: C10H6O5 (206.0215226)

CAS ID:

cyclic dehypoxanthinylfutalosinate(1-)

Formula: C14H13O7 (293.0661248)

CAS ID:

dehypoxanthine futalosinate

Formula: C14H15O7 (295.081774)

CAS ID:

aminodeoxyfutalosinate

Formula: C19H18N5O6 (412.1257028)

CAS ID:

1,4-dihydroxy-6-naphthoate

Formula: C11H7O4 (203.0344322)

CAS ID:

adenosine 5'-monophosphate(2-)

Formula: C10H12N5O7P (345.0474332)

CAS ID:



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)


Pathway Source

Organism Taxonomy Group Enzyme List Source Ratio
Streptomyces coelicolor A3(2) MAGs 1.21.98.1 / 2.5.1.120 / 3.2.2.26 / 3.5.4.40 / 4.1.99.29 / 4.2.1.151 100.00%
Streptomyces albogriseolus bacteria 1.21.98.1 / 2.5.1.120 / 3.2.2.26 / 3.5.4.40 / 4.2.1.151 83.33%
Streptomyces halstedii bacteria 1.21.98.1 / 2.5.1.120 / 3.2.2.26 / 4.1.99.29 / 4.2.1.151 83.33%
Actinacidiphila oryziradicis bacteria 1.21.98.1 / 2.5.1.120 / 3.2.2.26 / 4.1.99.29 / 4.2.1.151 83.33%
Streptomyces wadayamensis bacteria 1.21.98.1 / 3.2.2.26 / 4.1.99.29 / 4.2.1.151 66.67%
Thermus thermophilus HB8 MAGs 2.5.1.120 / 3.2.2.26 / 4.1.99.29 / 4.2.1.151 66.67%
Thermus thermophilus HB27 MAGs 1.21.98.1 / 3.2.2.26 33.33%
Campylobacter lari RM2100 MAGs 1.21.98.1 / 4.2.1.151 33.33%
Acidothermus cellulolyticus 11B MAGs 3.2.2.26 / 3.5.4.40 33.33%
Streptomyces avermitilis MA-4680 = NBRC 14893 MAGs 3.5.4.40 16.67%
Deinococcus radiodurans R1 = ATCC 13939 = DSM 20539 MAGs 3.5.4.40 16.67%
Halalkalibacterium halodurans C-125 MAGs 1.21.98.1 16.67%
Campylobacter jejuni subsp. jejuni 81-176 MAGs 4.2.1.151 16.67%
Nitratiruptor sp. SB155-2 bacteria 3.5.4.40 16.67%