1,4-dihydroxy-6-naphthoate biosynthesis II

Mahanta N, Fedoseyenko D, Dairi T, Begley TP. Menaquinone biosynthesis: formation of aminofutalosine requires a unique radical SAM enzyme. J Am Chem Soc. 2013 Oct 16;135(41):15318–21. PMID: 24083939; PMCID: PMC3855536.; 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

Adenine

Formula: C5H5N5 (135.054493)

CAS ID: 73-24-5

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



Enzyme

EC Number name full name note
1.21.98.1 cyclic dehypoxanthinyl futalosine synthase dehypoxanthine futalosine:S-adenosyl-L-methionine oxidoreductase (cyclizing)
3.2.2.30 aminodeoxyfutalosine nucleosidase 6-amino-6-deoxyfutalosine ribohydrolase
3.2.2.9 adenosylhomocysteine nucleosidase S-adenosyl-L-homocysteine homocysteinylribohydrolase


Pathway Source

Organism Taxonomy Group Enzyme List Source Ratio
Helicobacter pylori J99 MAGs 3.2.2.30 / 3.2.2.9 66.67%
Helicobacter pylori 26695 MAGs 3.2.2.30 / 3.2.2.9 66.67%
Campylobacter jejuni subsp. jejuni NCTC 11168 = ATCC 700819 MAGs 3.2.2.30 / 3.2.2.9 66.67%
Thermus thermophilus HB27 MAGs 1.21.98.1 / 3.2.2.9 66.67%
Streptomyces albogriseolus bacteria 1.21.98.1 / 3.2.2.9 66.67%
Halalkalibacterium halodurans C-125 MAGs 1.21.98.1 / 3.2.2.9 66.67%
Campylobacter lari RM2100 MAGs 1.21.98.1 / 3.2.2.9 66.67%
Shewanella sp. MR-4 bacteria 3.2.2.9 33.33%
Mycobacterium tuberculosis CDC1551 MAGs 3.2.2.9 33.33%
Haemophilus influenzae Rd KW20 MAGs 3.2.2.9 33.33%
Shouchella clausii KSM-K16 MAGs 3.2.2.9 33.33%
Paraburkholderia graminis bacteria 3.2.2.9 33.33%
Shewanella sp. MR-7 MAGs 3.2.2.9 33.33%
Vibrio campbellii ATCC BAA-1116 MAGs 3.2.2.9 33.33%
Aeromonas salmonicida subsp. salmonicida MAGs 3.2.2.9 33.33%
Oryza sativa plant 3.2.2.9 33.33%
Streptomyces halstedii bacteria 1.21.98.1 33.33%
Bacillus anthracis bacteria 3.2.2.9 33.33%
Aliivibrio fischeri bacteria 3.2.2.9 33.33%
Yersinia pestis bacteria 3.2.2.9 33.33%