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IUBMB Comments Binds a [4Fe-4S] cluster that is coordinated by 3 cysteines and an exchangeable S -adenosyl-L -methionine molecule. The first stage of catalysis is reduction of the S -adenosyl-L -methionine to produce methionine and a 5-deoxyadenosin-5-yl radical that is crucial for the conversion of the substrate. The reductant is assumed to be NADPH, which is provided by a flavoprotein:NADPH oxidoreductase system . Part of the pathway for thiamine biosynthesis.
The expected taxonomic range for this enzyme is: Bacteria, Archaea
Synonyms thiH , more
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thiH
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L-tyrosine + S-adenosyl-L-methionine + NADPH = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + NADP+ + H+
L-tyrosine + S-adenosyl-L-methionine + NADPH = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + NADP+ + H+
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L-tyrosine + S-adenosyl-L-methionine + NADPH = 2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + NADP+ + H+
ThiH is a member of the radical-S-adenosyl-L-methionine family. Proposed mechanism of ThiH-dependent cleavage of L-tyrosine: S-adenosyl-L-methionine is reductively cleaved to yield a highly reactive 5'-deoxyadenosyl radical. This radical is proposed to abstract the phenolic hydrogen atom from tyrosine, and the resultant substrate radical cleaves to yield dehydroglycine, which is required by ThiG for the thiazole cyclization reaction
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MetaCyc
thiazole component of thiamine diphosphate biosynthesis I
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L-tyrosine 4-methylphenol-lyase (2-iminoacetate-forming)
Binds a [4Fe-4S] cluster that is coordinated by 3 cysteines and an exchangeable S-adenosyl-L-methionine molecule. The first stage of catalysis is reduction of the S-adenosyl-L-methionine to produce methionine and a 5-deoxyadenosin-5-yl radical that is crucial for the conversion of the substrate. The reductant is assumed to be NADPH, which is provided by a flavoprotein:NADPH oxidoreductase system [4]. Part of the pathway for thiamine biosynthesis.
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L-tyrosine + S-adenosyl-L-methionine + reduced acceptor
2-iminoacetate + 4-methylphenol + 5'-deoxyadenosine + L-methionine + acceptor + 2 H+
Substrates: the reductive cleavage of S-adenosyl-L-methionine yields the highly reactive 5'-deoxyadenosyl radical, which can abstract the phenolic hydrogen atom from tyrosine Products: -
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iron-sulfur centre
contains an oxygen labile Fe-S cluster
[4Fe-4S]-center
essential for activity
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Iron
iron content is 5.2 mol eq of iron per mol of ThiH, contains an 4F-4S cluster essential for activity
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SwissProt
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SwissProt
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SwissProt
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Highest Expressing Human Cell Lines
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physiological function
involved in the biosynthesis of the thiazole moiety of thiamine
physiological function
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the enzyme complex ThiGH is involved in the rate-limiting step of thiamine biosynthesis
physiological function
the enzyme is essential for thiazole biosynthesis in Escherichia coli
physiological function
the enzyme is required for the synthesis of the 4-methyl-5-hydroxyethyl-thiazole monophosphate moiety of thiamine diphosphate
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additional information
the 440000 Da complex contains both ThiG and ThiH-His
44143
x * 44143, calculated from sequence
44143
x * 44143, electrospray mass spectrometry
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x * 44143, calculated from sequence
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x * 44143, electrospray mass spectrometry
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A26G
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
A272V
the thiH mutant allele results in a thiH null phenotype
A373P
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
A50T
the thiH mutant allele results in a thiH null phenotype
A51V
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
A61A
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
A61T
the thiH mutant allele results in a thiH null phenotype
C285A
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
C285H
the thiH mutant allele results in a thiH null phenotype
C89A
the thiH mutant allele results in a thiH null phenotype
D41V
the thiH mutant allele results in a thiH null phenotype
D6E
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
E131A
the thiH mutant allele results in a thiH null phenotype
E131K
the thiH mutant allele results in a thiH null phenotype
E187D
the thiH mutant allele results in a thiH null phenotype
E29K
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
E55G
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
E55K
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
G130A
the thiH mutant allele results in a thiH null phenotype
G216C
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
G22V
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
G327C
the thiH mutant allele results in a thiH null phenotype
h124Y
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
N87A
the thiH mutant allele results in a thiH null phenotype
N87K
the thiH mutant allele results in a thiH null phenotype
P334Q
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
P347S
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
Q338L
the thiH mutant allele results in a thiH null phenotype
R102P
the thiH mutant allele results in a thiH null phenotype
R205W
the thiH mutant allele results in a thiH null phenotype
T266N
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
V257A
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
V360I
the thiH mutant allele results in a phenotype with thiamine auxotrophy that is corrected by either L-tyrosine or thiazole
W363C
the thiH mutant allele results in a thiH null phenotype
Y190C
the thiH mutant allele results in a thiH null phenotype
Y91A
the thiH mutant allele results in a thiH null phenotype
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when isolated under anaerobic conditions, ThiG and ThiH-His co-purify as a large multimeric non-covalent complex
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C-terminally hexahistidine-tagged ThiH(ThiH-His) is expressed in Escherichia coli as a soluble protein from thiGHHis-tag and thiFSGH-His-tag-bearing plasmids
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Kriek, M.; Martins, F.; Challand, M.R.; Croft, A.; Roach, P.L.
Thiamine biosynthesis in Escherichia coli: identification of the intermediate and by-product derived from tyrosine
Angew. Chem. Int. Ed. Engl.
46
9223-9226
2007
Escherichia coli (P30140)
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Leonardi, R.; Fairhurst, S.A.; Kriek, M.; Lowe, D.J.; Roach, P.L.
Thiamine biosynthesis in Escherichia coli: isolation and initial characterisation of the ThiGH complex
FEBS Lett.
539
95-99
2003
Escherichia coli (P30140)
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Leonardi, R.; Roach, P.L.
Thiamine biosynthesis in Escherichia coli: in vitro reconstitution of the thiazole synthase activity
J. Biol. Chem.
279
17054-17062
2004
Escherichia coli
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Martinez-Gomez, N.C.; Robers, M.; Downs, D.M.
Mutational analysis of ThiH, a member of the radical S-adenosylmethionine (AdoMet) protein superfamily
J. Biol. Chem.
279
40505-40510
2004
Salmonella enterica subsp. enterica serovar Typhimurium (Q9S498)
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Kriek, M.; Martins, F.; Leonardi, R.; Fairhurst, S.A.; Lowe, D.J.; Roach, P.L.
Thiazole synthase from Escherichia coli: an investigation of the substrates and purified proteins required for activity in vitro
J. Biol. Chem.
282
17413-17423
2007
Escherichia coli (P30140)
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