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Literature summary extracted from

  • Hu, W.; Song, H.; Sae Her, A.; Bak, D.W.; Naowarojna, N.; Elliott, S.J.; Qin, L.; Chen, X.; Liu, P.
    Bioinformatic and biochemical characterizations of C-S bond formation and cleavage enzymes in the fungus Neurospora crassa ergothioneine biosynthetic pathway (2014), Org. Lett., 16, 5382-5385.
    View publication on PubMedView publication on EuropePMC

Application

EC Number Application Comment Organism
1.21.3.10 biotechnology the Neurospora crassa ergothioneine biosynthetic pathway may be a more suitable platform than the mycobacterial one for ergothioneine production through metabolic engineering because the ergothioneine and glutathione biosynthetic pathways are uncoupled and they do not compete with each other anymore in Neurospora crassa Neurospora crassa

Cloned(Commentary)

EC Number Cloned (Comment) Organism
1.14.99.50 recombinant overexpression of Strep-tagged enzyme in Escherichia coli Mycolicibacterium smegmatis
1.21.3.10 gene egt1, overexpression in Escherichia coli strain BL21(DE3) from pASK-IBA3+ vector Neurospora crassa

KM Value [mM]

EC Number KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
1.21.3.10 0.39
-
 hercynine with gamma-L-glutamyl-L-cysteine, pH and temperature not specified in the publication Neurospora crassa
1.21.3.10 0.436
-
 hercynine with L-Cys, pH and temperature not specified in the publication Neurospora crassa
1.21.3.10 0.603
-
 L-cysteine pH and temperature not specified in the publication Neurospora crassa
1.21.3.10 7.68
-
 gamma-L-glutamyl-L-cysteine pH and temperature not specified in the publication Neurospora crassa

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
1.14.99.50 Fe2+ a mononuclear non-heme iron enzyme Mycolicibacterium smegmatis
1.21.3.10 Fe2+ a non-heme iron enzyme, that contains about 0.90 Fe per Egt1 monomer Neurospora crassa

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2 Mycolicibacterium smegmatis
-
 gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2 Mycolicibacterium smegmatis the enzyme is extremely specific in terms of substrate specificity gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2 Mycolicibacterium smegmatis ATCC 700084
-
 gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2 Mycolicibacterium smegmatis ATCC 700084 the enzyme is extremely specific in terms of substrate specificity gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.21.3.10 hercynine + L-cysteine + O2 Neurospora crassa
-
 S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.21.3.10 hercynine + L-cysteine + O2 Neurospora crassa ATCC 24698
-
 S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
1.14.99.50 Mycolicibacterium smegmatis A0R5N0 gene egtB
-
1.14.99.50 Mycolicibacterium smegmatis ATCC 700084 A0R5N0 gene egtB
-
1.21.3.10 Neurospora crassa Q7RX33 gene egt1
-
1.21.3.10 Neurospora crassa ATCC 24698 Q7RX33 gene egt1
-

Purification (Commentary)

EC Number Purification (Comment) Organism
1.14.99.50 recombinant Strep-tagged enzyme from Escherichia coli by affinity chromatography Mycolicibacterium smegmatis

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2
-
 Mycolicibacterium smegmatis gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2 the enzyme is extremely specific in terms of substrate specificity Mycolicibacterium smegmatis gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2
-
 Mycolicibacterium smegmatis ATCC 700084 gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.14.99.50 hercynine + gamma-L-glutamyl-L-cysteine + O2 the enzyme is extremely specific in terms of substrate specificity Mycolicibacterium smegmatis ATCC 700084 gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.21.3.10 hercynine + gamma-L-glutamyl-L-cysteine + O2 reaction of EC 1.14.99.50, enzyme Egt1 has about 62fold greater specificity (kobs/Km) for L-cysteine relative to gamma-Glu-Cys Neurospora crassa gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.21.3.10 hercynine + gamma-L-glutamyl-L-cysteine + O2 reaction of EC 1.14.99.50, enzyme Egt1 has about 62fold greater specificity (kobs/Km) for L-cysteine relative to gamma-Glu-Cys Neurospora crassa ATCC 24698 gamma-L-glutamyl-S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.21.3.10 hercynine + L-cysteine + O2
-
 Neurospora crassa S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.21.3.10 hercynine + L-cysteine + O2
-
 Neurospora crassa ATCC 24698 S-(hercyn-2-yl)-L-cysteine S-oxide + H2O
-
 ?
1.21.3.10 additional information usage of three different assays, when histidine and cysteine are the substrates (cf. EC 1.14.99.52), kobs is at least 100fold less than the case using the Cys and hercynine combination, and when gamma-Glu-Cys and hercynine are the substrates (cf. EC 1.14.99.50), the activity is low compared to the native substrates, and when gamma-Glu-Cys and histidine are the substrates, similar to the case of histidine and cysteine combination, the rate is close to background level, overview Neurospora crassa ?
-
 ?
1.21.3.10 additional information usage of three different assays, when histidine and cysteine are the substrates (cf. EC 1.14.99.52), kobs is at least 100fold less than the case using the Cys and hercynine combination, and when gamma-Glu-Cys and hercynine are the substrates (cf. EC 1.14.99.50), the activity is low compared to the native substrates, and when gamma-Glu-Cys and histidine are the substrates, similar to the case of histidine and cysteine combination, the rate is close to background level, overview Neurospora crassa ATCC 24698 ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
1.14.99.50 EgtB
-
 Mycolicibacterium smegmatis
1.21.3.10 Egt1
-
 Neurospora crassa

Turnover Number [1/s]

EC Number Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
1.21.3.10 0.46
-
 hercynine with gamma-L-glutamyl-L-cysteine, pH and temperature not specified in the publication Neurospora crassa
1.21.3.10 2.27
-
 hercynine with L-Cys, pH and temperature not specified in the publication Neurospora crassa

General Information

EC Number General Information Comment Organism
1.14.99.50 evolution the two known sulfoxide synthases EgtB and OvoA distinguish themselves from each other by their substrate preferences and product C-S bond regioselectivity Mycolicibacterium smegmatis
1.14.99.50 metabolism the enzyme catalyzes a step in the ergothioneine biosynthetic pathway, overview Mycolicibacterium smegmatis
1.14.99.50 metabolism the enzyme is involved in the ergothioneine biosynthesis catalyzing a direct four-electron oxidative process, coupling between hercynine and gamma-L-glutamyl-L-cysteine, overview Mycolicibacterium smegmatis
1.21.3.10 metabolism the enzyme catalyzes a step in the ergothioneine biosynthetic pathway, with the oxidative C-S bond formation and the subsequent C-S bond cleavage reaction, which result in a net transfer of the sulfur atom form cysteine to histidine imidazole side-chain, overview. The fungus Neurospora crassa has a more concise ergothioneine biosynthetic pathway because its nonheme iron enzyme, Egt1, makes use of cysteine instead of gamma-Glu-Cys as the substrate. Such a change of substrate preference eliminates the competition between ergothioneine and glutathione biosyntheses Neurospora crassa