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EC Tree
IUBMB Comments The enzyme catalyses the irreversible aromatization of the thiazole moiety of 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate.
The expected taxonomic range for this enzyme is: Bacteria, Archaea
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tenI
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2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate = 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate = 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
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2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate = 2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
reaction mechanism, overview
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2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate isomerase
The enzyme catalyses the irreversible aromatization of the thiazole moiety of 2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate.
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2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate
2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate
2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
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ir
2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate
2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
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reversibility analysis by NMR
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ir
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2-[(2R,5Z)-2-carboxy-4-methylthiazol-5(2H)-ylidene]ethyl phosphate
2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate
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ir
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gene tenI
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brenda
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metabolism
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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
physiological function
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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
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TENI_BACSU
Bacillus subtilis (strain 168)
205
0
22929
Swiss-Prot
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A0A7W3LDZ1_9BACI
205
0
22861
TrEMBL
-
A0A2H5UXN8_9ARCH
203
0
21408
TrEMBL
-
S7SW30_9BACI
210
0
22137
TrEMBL
-
A0A7W8JCC8_9BACI
204
0
22956
TrEMBL
-
A0A650LSU6_9CLOT
212
0
23532
TrEMBL
-
A0A7W8IRC4_9BACI
200
0
21453
TrEMBL
-
A0A7W7TRV6_9BACI
206
0
22920
TrEMBL
-
S6FX14_9BACI
205
0
22804
TrEMBL
-
A0A4P6LWY5_9FIRM
194
0
20904
TrEMBL
-
A0A7W0BXF9_9BACI
209
0
22885
TrEMBL
-
A0A6J4N7Q7_9ACTN
uncultured Nocardioides sp
186
0
19691
TrEMBL
-
A0A7X0D9F3_9BACI
204
0
22558
TrEMBL
-
A0A5C0WCQ3_BACIA
200
0
21946
TrEMBL
-
A0A7W6ARR5_9BACI
209
0
22222
TrEMBL
-
A0A7J0ARI9_9BACT
171
0
18928
TrEMBL
-
A0A653P339_9BACI
210
0
23389
TrEMBL
-
A0A498U113_BACIA
200
0
21967
TrEMBL
-
A0A7X0EFZ5_9BACI
203
0
21434
TrEMBL
-
A0A7J0BAC9_9BACT
201
0
22171
TrEMBL
-
A0A509G229_PAEPO
197
0
21030
TrEMBL
-
A0A494WU79_CLOS5
Clostridium scindens (strain ATCC 35704 / DSM 5676 / VPI 13733 / 19)
196
0
21561
TrEMBL
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A0A165B6B2_BACIU
205
0
22914
TrEMBL
-
A0A1E3LAV1_9BACL
211
0
23349
TrEMBL
-
A0A7W3NFD4_9BACI
207
0
22298
TrEMBL
-
A0A0B5SHM9_BACMY
206
0
22637
TrEMBL
-
A0A2H5ZXW3_9BACT
145
0
15247
TrEMBL
-
A0A653T2W8_9BACI
205
0
21898
TrEMBL
-
A0A5C8IVU4_BACAM
205
0
22628
TrEMBL
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A0A6L5B6G8_9BACI
202
0
22202
TrEMBL
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A0A7U9S328_9FIRM
256
0
28129
TrEMBL
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A0A645HZN4_9ZZZZ
91
0
9636
TrEMBL
other Location (Reliability: 3 )
E0RAR3_PAEP6
Paenibacillus polymyxa (strain E681)
197
0
21075
TrEMBL
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A0A0K2XEE9_HELHE
190
0
20986
TrEMBL
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A0A411A4L0_9BACI
205
0
22834
TrEMBL
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A0A7W0BZT0_9BACI
208
0
22670
TrEMBL
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A0A3A2YUX1_BACCE
206
0
22805
TrEMBL
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A0A7W0C1L5_9BACI
204
0
23024
TrEMBL
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A0A800N8B1_CYTFI
204
0
22171
TrEMBL
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A0A7U9S1W7_9FIRM
208
0
22452
TrEMBL
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A0A7W3SUG3_9BACL
201
0
22057
TrEMBL
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A0A7H2CFX8_9BACI
205
0
22776
TrEMBL
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A0A0K2XQ20_HELHE
201
0
22298
TrEMBL
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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
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recombinant His-tagged TenI from Escherichia coli strain BL21(DE3) by nickel affinity chromatography
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gene tenI, overexpression as His-tagged enzyme in Escherichia coli strain BL21(DE3)
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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
J. Am. Chem. Soc.
133
9311-9319
2011
Bacillus subtilis
brenda
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