The Enzyme Database

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EC 1.14.99.50     
Accepted name: γ-glutamyl hercynylcysteine S-oxide synthase
Reaction: hercynine + γ-L-glutamyl-L-cysteine + O2 = γ-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
For diagram of ergothioneine and ovothiol biosynthesis, click here
Glossary: hercynine = Nα,Nα,Nα-trimethyl-L-histidine
Other name(s): EgtB
Systematic name: hercynine,γ-L-glutamyl-L-cysteine:oxygen oxidoreductase [γ-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide-forming]
Comments: Requires Fe2+ for activity. The enzyme, found in bacteria, is specific for both hercynine and γ-L-glutamyl-L-cysteine. It is part of the biosynthesis pathway of ergothioneine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Seebeck, F.P. In vitro reconstitution of mycobacterial ergothioneine biosynthesis. J. Am. Chem. Soc. 132 (2010) 6632–6633. [DOI] [PMID: 20420449]
2.  Pluskal, T., Ueno, M. and Yanagida, M. 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 (2014). [DOI] [PMID: 24828577]
[EC 1.14.99.50 created 2015]
 
 
EC 1.14.99.51     
Accepted name: hercynylcysteine S-oxide synthase
Reaction: hercynine + L-cysteine + O2 = S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
For diagram of ergothioneine and ovothiol biosynthesis, click here
Glossary: hercynine = Nα,Nα,Nα-trimethyl-L-histidine
Other name(s): Egt1; Egt-1
Systematic name: hercynine,L-cysteine:oxygen [S-(hercyn-2-yl)-L-cysteine S-oxide-forming]
Comments: Requires Fe2+ for activity. The enzyme, found in fungal species, is part of a fusion protein that also has the the activity of EC 2.1.1.44, L-histidine Nα-methyltransferase. It is part of the biosynthesis pathway of ergothioneine. The enzyme can also use L-selenocysteine to produce hercynylselenocysteine, which can be converted to selenoneine.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Pluskal, T., Ueno, M. and Yanagida, M. 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 (2014). [DOI] [PMID: 24828577]
[EC 1.14.99.51 created 2015]
 
 
EC 3.5.1.118     
Accepted name: γ-glutamyl hercynylcysteine S-oxide hydrolase
Reaction: γ-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O = S-(hercyn-2-yl)-L-cysteine S-oxide + L-glutamate
For diagram of ergothioneine and ovothiol biosynthesis, click here
Glossary: hercynine = Nα,Nα,Nα-trimethyl-L-histidine = 3-(1H-imidazol-5-yl)-2-(trimethylamino)propanoate
S-(hercyn-2-yl)-L-cysteine S-oxide = S-(N,N,N-trimethyl-L-histidin-2-yl)-L-cysteine S-oxide
Other name(s): EgtC
Systematic name: γ-glutamyl-S-(hercyn-2-yl)cysteine S-oxide amidohydrolase
Comments: The enzyme is part of the biosynthesis pathway of ergothioneine in mycobacteria.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Seebeck, F.P. In vitro reconstitution of mycobacterial ergothioneine biosynthesis. J. Am. Chem. Soc. 132 (2010) 6632–6633. [DOI] [PMID: 20420449]
[EC 3.5.1.118 created 2015]
 
 
EC 4.4.1.36     
Accepted name: hercynylcysteine S-oxide lyase
Reaction: S-(hercyn-2-yl)-L-cysteine S-oxide + reduced acceptor = ergothioneine + pyruvate + NH3 + acceptor (overall reaction)
(1a) S-(hercyn-2-yl)-L-cysteine S-oxide + H2O = 2-(hydroxysulfanyl)hercynine + pyruvate + NH3
(1b) 2-(hydroxysulfanyl)hercynine + reduced acceptor = ergothioneine + acceptor + H2O (spontaneous)
Glossary: 2-(hydroxysulfanyl)hercynine = Nα,Nα,Nα-trimethyl-2-(hydroxysulfanyl)-L-histidine = 2-sulfenohercynine
ergothioneine = Nα,Nα,Nα-trimethyl-2-sulfanylidene-2,3-dihydro-L-histidine
Other name(s): egtE (gene name)
Systematic name: S-(hercyn-2-yl)-L-cysteine ergothioneine-hydroxysulfanolate-lyase
Comments: Contains pyridoxal 5′-phosphate. 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.
Links to other databases: BRENDA, EXPASY, KEGG, MetaCyc
References:
1.  Seebeck, F.P. In vitro reconstitution of mycobacterial ergothioneine biosynthesis. J. Am. Chem. Soc. 132 (2010) 6632–6633. [DOI] [PMID: 20420449]
2.  Pluskal, T., Ueno, M. and Yanagida, M. 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 (2014). [DOI] [PMID: 24828577]
3.  Song, H., Hu, W., Naowarojna, N., Her, A.S., Wang, S., Desai, R., Qin, L., Chen, X. and Liu, P. Mechanistic studies of a novel C-S lyase in ergothioneine biosynthesis: the involvement of a sulfenic acid intermediate. Sci. Rep. 5:11870 (2015). [DOI] [PMID: 26149121]
[EC 4.4.1.36 created 2017]
 
 


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