ExplorEnz: EC 4.4.1.36

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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 = N^α,N^α,N^α-trimethyl-2-(hydroxysulfanyl)-L-histidine = 2-sulfenohercynine
ergothioneine = N^α,N^α,N^α-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, Gene, 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]