Reaction: cyclic dehypoxanthine futalosine = 5,8-dihydroxy-2-naphthoate + dihydroxyacetone
For diagram of reaction 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, CAS registry number:
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. [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. [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. [PMID: 34143602]