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1.21.98.1

Accepted name:

cyclic dehypoxanthinyl futalosine synthase

Reaction:

dehypoxanthine futalosine + S-adenosyl-L-methionine = cyclic dehypoxanthinyl futalosine + 5′-deoxyadenosine + L-methionine

For diagram of the futalosine pathway, click here

Glossary:

dehypoxanthine futalosine = 3-{3-[(2R,3S,4R)-3,4,5-trihydroxytetrahydrofuran-2-yl]propanoyl}benzoate
cyclic dehypoxanthinyl futalosine = (2R,3S,4R)-3,4,5-trihydroxy-4′-oxo-3′,4,4′,5-tetrahydro-2’H,3H-spiro[furan-2,1′-naphthalene]-6′-carboxylate

Other name(s):

MqnC; dehypoxanthinyl futalosine cyclase

Systematic name:

dehypoxanthine futalosine:S-adenosyl-L-methionine oxidoreductase (cyclizing)

Comments:

This enzyme is a member of the ‘AdoMet radical’ (radical SAM) family. The enzyme, found in several bacterial species, is part of the futalosine pathway for menaquinone biosynthesis.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Hiratsuka, T., Furihata, K., Ishikawa, J., Yamashita, H., Itoh, N., Seto, H. and Dairi, T. An alternative menaquinone biosynthetic pathway operating in microorganisms. Science 321 (2008) 1670–1673. [DOI] [PMID: 18801996]
2.	Cooper, L.E., Fedoseyenko, D., Abdelwahed, S.H., Kim, S.H., Dairi, T. and Begley, T.P. In vitro reconstitution of the radical S-adenosylmethionine enzyme MqnC involved in the biosynthesis of futalosine-derived menaquinone. Biochemistry 52 (2013) 4592–4594. [DOI] [PMID: 23763543]

[EC 1.21.98.1 created 2014 as EC 1.21.99.2, transferred 2014 to EC 1.21.98.1]

1.21.99.2

Transferred entry:

EC 1.21.99.2, cyclic dehypoxanthinyl futalosine synthase. Now classified as EC 1.21.98.1, cyclic dehypoxanthinyl futalosine synthase.

[EC 1.21.99.2 created 2014, deleted 2014]

3.2.2.26

Accepted name:

futalosine hydrolase

Reaction:

futalosine + H₂O = dehypoxanthine futalosine + hypoxanthine

For diagram of the futalosine pathway, click here

Glossary:

futalosine = 3-(3-((3S,4R)-3,4-dihydroxy-5-(6-oxo-3H-purin-9(6H)-yl)tetrahydrofuran-2-yl)propanoyl)benzoate
dehypoxanthine futalosine = 7-(3-carboxyphenyl)-D-ribo-7-dehydro-5,6-dideoxyheptose

Other name(s):

futalosine nucleosidase; MqnB (ambiguous)

Systematic name:

futalosine ribohydrolase

Comments:

This enzyme, which is specific for futalosine, catalyses the second step of a novel menaquinone biosynthetic pathway that is found in some prokaryotes.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Hiratsuka, T., Furihata, K., Ishikawa, J., Yamashita, H., Itoh, N., Seto, H. and Dairi, T. An alternative menaquinone biosynthetic pathway operating in microorganisms. Science 321 (2008) 1670–1673. [DOI] [PMID: 18801996]

[EC 3.2.2.26 created 2008]

3.2.2.30

Accepted name:

aminodeoxyfutalosine nucleosidase

Reaction:

6-amino-6-deoxyfutalosine + H₂O = dehypoxanthine futalosine + adenine

For diagram of the futalosine pathway, click here

Glossary:

6-amino-6-deoxyfutalosine = 3-{3-[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]propanoyl}benzoate
dehypoxanthine futalosine = 3-{3-[(2R,3S,4R)-3,4,5-trihydroxytetrahydrofuran-2-yl]propanoyl}benzoate

Other name(s):

AFL nucleosidase; aminofutalosine nucleosidase; methylthioadenosine nucleosidase; MqnB (ambiguous)

Systematic name:

6-amino-6-deoxyfutalosine ribohydrolase

Comments:

The enzyme, found in several bacterial species, catalyses a step in a modified futalosine pathway for menaquinone biosynthesis. While the enzyme from some organisms also has the activity of EC 3.2.2.9, adenosylhomocysteine nucleosidase, the enzyme from Chlamydia trachomatis is specific for 6-amino-6-deoxyfutalosine [7].

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc, PDB

References:

1.	Hiratsuka, T., Furihata, K., Ishikawa, J., Yamashita, H., Itoh, N., Seto, H. and Dairi, T. An alternative menaquinone biosynthetic pathway operating in microorganisms. Science 321 (2008) 1670–1673. [DOI] [PMID: 18801996]
2.	Li, X., Apel, D., Gaynor, E.C. and Tanner, M.E. 5′-methylthioadenosine nucleosidase is implicated in playing a key role in a modified futalosine pathway for menaquinone biosynthesis in Campylobacter jejuni. J. Biol. Chem. 286 (2011) 19392–19398. [DOI] [PMID: 21489995]
3.	Arakawa, C., Kuratsu, M., Furihata, K., Hiratsuka, T., Itoh, N., Seto, H. and Dairi, T. Diversity of the early step of the futalosine pathway. Antimicrob. Agents Chemother. 55 (2011) 913–916. [DOI] [PMID: 21098241]
4.	Wang, S., Haapalainen, A.M., Yan, F., Du, Q., Tyler, P.C., Evans, G.B., Rinaldo-Matthis, A., Brown, R.L., Norris, G.E., Almo, S.C. and Schramm, V.L. A picomolar transition state analogue inhibitor of MTAN as a specific antibiotic for Helicobacter pylori. Biochemistry 51 (2012) 6892–6894. [DOI] [PMID: 22891633]
5.	Mishra, V. and Ronning, D.R. Crystal structures of the Helicobacter pylori MTAN enzyme reveal specific interactions between S-adenosylhomocysteine and the 5′-alkylthio binding subsite. Biochemistry 51 (2012) 9763–9772. [DOI] [PMID: 23148563]
6.	Kim, R.Q., Offen, W.A., Davies, G.J. and Stubbs, K.A. Structural enzymology of Helicobacter pylori methylthioadenosine nucleosidase in the futalosine pathway. Acta Crystallogr. D Biol. Crystallogr. 70 (2014) 177–185. [DOI] [PMID: 24419390]
7.	Barta, M.L., Thomas, K., Yuan, H., Lovell, S., Battaile, K.P., Schramm, V.L. and Hefty, P.S. Structural and biochemical characterization of Chlamydia trachomatis hypothetical protein CT263 supports that menaquinone synthesis occurs through the futalosine pathway. J. Biol. Chem. 289 (2014) 32214–32229. [DOI] [PMID: 25253688]

[EC 3.2.2.30 created 2014]

4.1.99.29

Accepted name:

5,8-dihydroxy-2-naphthoate synthase

Reaction:

cyclic dehypoxanthine futalosine = 5,8-dihydroxy-2-naphthoate + dihydroxyacetone

For diagram of the futalosine pathway, click here

Glossary:

cyclic dehypoxanthine futalosine = (1R,3′S,4′R)-3′,4′,5′-trihydroxy-4-oxo-2,3-dihydrospiro[naphthalene-1,2′-oxolane]-6-carboxylate
5,8-dihydroxy-2-naphthoate = 5,8-dihydroxynaphthalene-2-carboxylate

Other name(s):

mqnD (gene name); 1,4-dihydroxy-6-naphthoate synthase (incorrect)

Systematic name:

cyclic dehypoxanthine futalosine lyase (dihydroxyacetone-forming)

Comments:

The enzyme participates in alternative menaquinone biosynthesis pathways known as the futalosine and modified futalosine pathways, which occurs in some bacterial species including several human pathogens such as Helicobacter pylori, Campylobacter jejuni, and Chlamydia.

Links to other databases:

BRENDA, EXPASY, KEGG, MetaCyc

References:

1.	Hiratsuka, T., Furihata, K., Ishikawa, J., Yamashita, H., Itoh, N., Seto, H. and Dairi, T. An alternative menaquinone biosynthetic pathway operating in microorganisms. Science 321 (2008) 1670–1673. [DOI] [PMID: 18801996]
2.	Arai, R., Murayama, K., Uchikubo-Kamo, T., Nishimoto, M., Toyama, M., Kuramitsu, S., Terada, T., Shirouzu, M. and Yokoyama, S. Crystal structure of MqnD (TTHA1568), a menaquinone biosynthetic enzyme from Thermus thermophilus HB8. J. Struct. Biol. 168 (2009) 575–581. [DOI] [PMID: 19602440]
3.	Manion-Sommerhalter, H.R., Fedoseyenko, D., Joshi, S. and Begley, T.P. Menaquinone biosynthesis: the mechanism of 5,8-dihydroxy-2-naphthoate synthase (MqnD). Biochemistry 60 (2021) 1947–1951. [DOI] [PMID: 34143602]

[EC 4.1.99.29 created 2024]