Reaction: 2 ATP + 2 3-(4-hydroxyphenyl)pyruvate = 2 AMP + 2 diphosphate + atromentin (overall reaction)
(1a) ATP + 3-(4-hydroxyphenyl)pyruvate + [atromentin synthase] = AMP + diphosphate + 3-(4-hydroxyphenyl)pyruvoyl-[atromentin synthase]
(1b) ATP + 3-(4-hydroxyphenyl)pyruvate + 3-(4-hydroxyphenyl)pyruvoyl-[atromentin synthase] = AMP + diphosphate + atromentin + [atromentin synthase]
For diagram of reaction click here.
Glossary: atromentin = 2,5-dihydroxy-3,6-bis(4-hydroxyphenyl)-1,4-benzoquinone
Other name(s): atromentin synthetase; invA1 (gene name); invA2 (gene name); invA5 (gene name); greA (gene name); atrA (gene name)
Systematic name: 3-(4-hydroxyphenyl)pyruvate:3-(4-hydroxyphenyl)pyruvate ligase (atromentin-forming)
Comments: Requires Mg2+.The enzyme, found in some fungi such as members of the Boletales and Eurotiales order, is a non-ribosomal peptide synthase-like enzyme comprising three domains - an adelylation (A) domain, an ayl-carrier protein (ACP) domain, and a thioesterase (TE) domain. The enzyme activates 3-(4-hydroxyphenyl)pyruvate by adenylation and catalyses the dimerization/cyclization of two such molecules to form atromentin. Atromentin is a precursor for assorted metabolites produced by the fungi, including pulvinic acids and 2,5-diarylcyclopentenones.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc, CAS registry number:
References:
1. Schneider, P., Bouhired, S. and Hoffmeister, D. Characterization of the atromentin biosynthesis genes and enzymes in the homobasidiomycete Tapinella panuoides. Fungal Genet. Biol. 45 (2008) 1487-1496. [PMID: 18805498]
2. Wackler, B., Lackner, G., Chooi, Y.H. and Hoffmeister, D. Characterization of the Suillus grevillei quinone synthetase GreA supports a nonribosomal code for aromatic α-keto acids. Chembiochem 13 (2012) 1798-1804. [PMID: 22730234]
3. Braesel, J., Gotze, S., Shah, F., Heine, D., Tauber, J., Hertweck, C., Tunlid, A., Stallforth, P. and Hoffmeister, D. Three redundant synthetases secure redox-active pigment production in the Basidiomycete Paxillus involutus. Chem. Biol. 22 (2015) 1325-1334. [PMID: 26496685]