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4.4.1.36 |
Description |
Hercynylcysteine S-oxide lyase |
Alternative names |
hercynylcysteine sulfoxide lyase;
EgtE (gene name) |
Catalyzed reaction |
S-(hercyn-2-yl)-L-cysteine S-oxide + reduced acceptor = ergothioneine + pyruvate + ammonia + acceptor (overall reaction)
(1a) S-(hercyn-2-yl)-L-cysteine S-oxide + H(2)O = 2-(hydroxysulfanyl)hercynine + pyruvate + NH(3).
(1b) 2-(hydroxysulfanyl)hercynine + reduced acceptor = ergothioneine + acceptor + H(2)O (spontaneous) |
Cofactor |
Pyridoxal phosphate. |
Comments |
The enzyme, characterized from the bacterium Mycobacterium smegmatis, cayalyses the last step in the pathway of ergothioneine biosynthesis. The enzyme forms a 2-(hydroxysulfanyl)hercynine intermediate, which is reduced to ergothioneine non-enzymically by a thiol. In vitro, DTT can serve this function.
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Ergothioneine is a a thiourea derivative of histidine. This small, sulfur-containing metabolite (229 Da) is synthesized by various species of bacteria and fungi, and can accumulate to millimolar levels in tissues or cells (e.g. erythrocytes) of higher eukaryotes. |
Organisms |
-Eubacteria -Fungi |
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Family |
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Links |
Enzyme (activities) 4.4.1.36
BRENDA (activities) 4.4.1.36
KEGG (pathways) 4.4.1.36
PLPMDB (PLP mutants) 4.4.1.36
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References |
Song H, Hu W, Naowarojna N, Her AS, Wang S, Desai R, Qin L, Chen X, Liu P (2015) Mechanistic studies of a novel C-S lyase in ergothioneine biosynthesis: the involvement of a sulfenic acid intermediate Sci Rep 7 11870. Hu W, Song H, Sae Her A, Bak DW, Naowarojna N, Elliott SJ, Qin L, Chen X, Liu P (2014) Bioinformatic and biochemical characterizations of C-S bond formation and cleavage enzymes in the fungus Neurospora crassa ergothioneine biosynthetic pathway Org Lett 16 5382-5. Pluskal T, Ueno M, Yanagida M (2014) Genetic and metabolomic dissection of the ergothioneine and selenoneine biosynthetic pathway in the fission yeast, S. pombe, and construction of an overproduction system PLoS One 9 e97774. Seebeck, F.P. (2010) In vitro reconstitution of mycobacterial ergothioneine biosynthesis J Am Chem Soc 132 6632-3. Articles on 4.4.1.36 |
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last changed |
2017/12/21 12:49 |
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