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Literature summary extracted from

  • Hazra, A.B.; Han, Y.; Chatterjee, A.; Zhang, Y.; Lai, R.Y.; Ealick, S.E.; Begley, T.P.
    A missing enzyme in thiamin thiazole biosynthesis: identification of TenI as a thiazole tautomerase (2011), J. Am. Chem. Soc., 133, 9311-9319.
    View publication on PubMedView publication on EuropePMC

Cloned(Commentary)

EC Number Cloned (Comment) Organism
5.3.99.10 gene tenI, overexpression as His-tagged enzyme in Escherichia coli strain BL21(DE3) Bacillus subtilis

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
5.3.99.10 enzyme TenI complexed with its reaction product cThz-P bound in the active site, hanging drop vapor diffusion method, liand-free TenI is grown from 1.65 to 1.75 M ammonium sulfate, 100 mM bicine, pH 8.7, 9.6, 2% PEG 400 w/v, and 8 mM L-cysteine, crystals are first dialyzed into 2.38 M sodium malonate, pH 7.0, to remove the sulfate ions by gradually increasing the sodium malonate concentration and decreasing the ammonium sulfate concentration, and soaked overnight in 2.38 M sodium malonate, 21.5 mM bicine, pH 9.0, 0.01% PEG400 w/v, 0.5 mM L-cysteine, 4% glycerol, and 11.5 mM cThz-P, X-ray diffraction structure determination and analysis Bacillus subtilis

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + (R,Z)-2-(2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate Bacillus subtilis
-
 diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the tautomerization and decarboxylation of the intermediate (2R,5Z)-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethylidene]-2,5-dihydro-1,3-thiazol-3-ium ?
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + (R,Z)-2-(2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate Bacillus subtilis 168
-
 diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the tautomerization and decarboxylation of the intermediate (2R,5Z)-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethylidene]-2,5-dihydro-1,3-thiazol-3-ium ?
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate Bacillus subtilis
-
 diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the decarboxylation of the intermediate 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium ?
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate Bacillus subtilis 168
-
 diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the decarboxylation of the intermediate 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium ?
5.3.99.10 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate Bacillus subtilis
-
 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
-
 ir

Organism

EC Number Organism UniProt Comment Textmining
2.5.1.3 Bacillus subtilis P39594
-
-
2.5.1.3 Bacillus subtilis 168 P39594
-
-
2.8.1.10 Bacillus subtilis O31618
-
-
5.3.99.10 Bacillus subtilis
-
 gene tenI
-

Purification (Commentary)

EC Number Purification (Comment) Organism
5.3.99.10 recombinant His-tagged TenI from Escherichia coli strain BL21(DE3) by nickel affinity chromatography Bacillus subtilis

Reaction

EC Number Reaction Comment Organism Reaction ID
5.3.99.10 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate = 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate reaction mechanism, overview Bacillus subtilis
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + (R,Z)-2-(2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate
-
 Bacillus subtilis diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the tautomerization and decarboxylation of the intermediate (2R,5Z)-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethylidene]-2,5-dihydro-1,3-thiazol-3-ium ?
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + (R,Z)-2-(2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate
-
 Bacillus subtilis 168 diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the tautomerization and decarboxylation of the intermediate (2R,5Z)-3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethylidene]-2,5-dihydro-1,3-thiazol-3-ium ?
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
-
 Bacillus subtilis diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the decarboxylation of the intermediate 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium ?
2.5.1.3 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
-
 Bacillus subtilis 168 diphosphate + thiamine phosphate + CO2 the enzyme catalyzes the decarboxylation of the intermediate 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-2-carboxy-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium ?
2.8.1.10 1-deoxy-D-xylulose 5-phosphate + 2-iminoacetate + thiocarboxy-adenylate-[sulfur-carrier protein ThiS]
-
 Bacillus subtilis 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate + [sulfur-carrier protein ThiS] + 2 H2O
-
 ?
5.3.99.10 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate
-
 Bacillus subtilis 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
-
 ir
5.3.99.10 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate reversibility analysis by NMR Bacillus subtilis 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
-
 ir

Synonyms

EC Number Synonyms Comment Organism
2.8.1.10 ThiG
-
 Bacillus subtilis
5.3.99.10 tenI
-
 Bacillus subtilis

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
5.3.99.10 7.6
-
 assay at Bacillus subtilis

General Information

EC Number General Information Comment Organism
2.8.1.10 physiological function reaction product of ThiG is a thiazole tautomer (R,Z)-2-(2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate, which is aromatized by tautomerase TenI to yield 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate Bacillus subtilis
5.3.99.10 metabolism TenI is involved in the thiamin thiazole biosynthesis. In Bacillus subtilis, the thiazole tautomer (R,Z)-2-(2-carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate is formed by an oxidative condensation of glycine, 1-deoxy-D-xylulose-5-phosphate, and cysteine Bacillus subtilis
5.3.99.10 physiological function TenI shows no thiamin phosphate synthase activity, but functionsas a thiazole tautomerase, substrates phosphate and histidine 122 act as the acid/base residues involved in catalysis, reaction mechanism, overview. TenI does not affect glycine oxidase, thiamin phosphate synthase, or ThiS-COSH formation Bacillus subtilis