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IUBMB CommentsA pyridoxal-phosphate protein, requiring K+. The enzyme cleaves a carbon-carbon bond, releasing indole and an unstable enamine product that tautomerizes to an imine form, which undergoes a hydrolytic deamination to form pyruvate and ammonia. The latter reaction, which can occur spontaneously, can also be catalysed by EC 3.5.99.10, 2-iminobutanoate/2-iminopropanoate deaminase. Also catalyses 2,3-elimination and beta-replacement reactions of some indole-substituted tryptophan analogues of L-cysteine, L-serine and other 3-substituted amino acids.
Synonyms
tryptophanase, tpase, tnase, trpase, tryptophan indole-lyase, l-tryptophanase, vctrpase, l-tryptophan indole-lyase, tryptophan indole lyase, tnaa2,
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L-tryptophan + H2O = indole + pyruvate + NH3
L-tryptophan + H2O = indole + pyruvate + NH3
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L-tryptophan + H2O = indole + pyruvate + NH3
mechanism
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L-tryptophan + H2O = indole + pyruvate + NH3
mechanism
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L-tryptophan + H2O = indole + pyruvate + NH3
in the reverse direction NH4+ interacts with bound pyridoxal 5'-phosphate to form an imine. Pyruvate is the second substrate, indole the third. alpha-Aminoacrylate functions as a common enzyme-bound intermediate in both synthetic and degradative reactions
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L-tryptophan + H2O = indole + pyruvate + NH3
mechanism that requires two catalytic bases
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L-tryptophan + H2O = indole + pyruvate + NH3
mechanism, solvent effects
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L-tryptophan + H2O = indole + pyruvate + NH3
reaction mechanism, overview
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L-tryptophan + H2O = indole + pyruvate + NH3
quinonoid intermediate formation involving Tyr71 and Cys298, mechanism, active site preorganization, overview
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L-tryptophan + H2O = indole + pyruvate + NH3
an active site base is essential for activity, and alpha-deuterated substrate exhibits modest primary isotope effects on kcat and kcat/Km, suggesting that substrate deprotonation is partially rate-limiting. Pre-steady state kinetics with enzyme TIL show rapid formation of an external aldimine intermediate, followed by deprotonation to give a quinonoid intermediate absorbing at about 500 nm. The mechanism of TIL requires both substrate strain and acid/base catalysis, and substrate strain is probably responsible for the very high substrate specificity of TIL. Acid-base catalysis mechanism of TIL, overview. The indole ring is preorganized into the active conformation before alpha-deprotonation occurs
L-tryptophan + H2O = indole + pyruvate + NH3
an active site base is essential for activity, and alpha-deuterated substrate exhibits modest primary isotope effects on kcat and kcat/Km, suggesting that substrate deprotonation is partially rate-limiting. Pre-steady state kinetics with enzyme TIL show rapid formation of external an aldimine intermediate, followed by deprotonation to give a quinonoid intermediate absorbing at about 500 nm. The mechanism of TIL requires both substrate strain and acid/base catalysis, and substrate strain is probably responsible for the very high substrate specificity of TIL. Acid-base catalysis mechanism of TIL, overview. The indole ring is preorganized into the active conformation before alpha-deprotonation occurs
L-tryptophan + H2O = indole + pyruvate + NH3
catalyses the reaction in which L-tryptophan is degraded to indole, pyruvate and ammonia via alpha,beta-elimination and beta-replacement mechanisms
L-tryptophan + H2O = indole + pyruvate + NH3
proposed mechanism of tryptophan indole-lyase, overview
L-tryptophan + H2O = indole + pyruvate + NH3
reaction via formation of quinonoid intermediate
L-tryptophan + H2O = indole + pyruvate + NH3
reaction mechanism, overview
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L-tryptophan indole-lyase (deaminating; pyruvate-forming)
A pyridoxal-phosphate protein, requiring K+. The enzyme cleaves a carbon-carbon bond, releasing indole and an unstable enamine product that tautomerizes to an imine form, which undergoes a hydrolytic deamination to form pyruvate and ammonia. The latter reaction, which can occur spontaneously, can also be catalysed by EC 3.5.99.10, 2-iminobutanoate/2-iminopropanoate deaminase. Also catalyses 2,3-elimination and beta-replacement reactions of some indole-substituted tryptophan analogues of L-cysteine, L-serine and other 3-substituted amino acids.
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2-oxindolyl-L-alanine + H2O
?
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?
4-methyl-Trp + H2O
?
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52% of the activity with L-Trp
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?
5-hydroxyindole + L-Cys
5-hydroxy-L-Trp + ?
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-
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?
5-hydroxyindole + S-methyl-L-Cys
5-hydroxy-L-Trp + ?
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-
-
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?
5-methylindole + L-Cys
5-methyl-L-Trp + ?
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-
-
-
?
5-methylindole + S-methyl-L-Cys
5-methyl-L-Trp + ?
-
-
-
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?
6-methyl-Trp + H2O
?
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44% of the activity with L-Trp
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?
alpha,beta-diaminopropionic acid
?
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?
beta-(benzimidazol-1-yl)-L-alanine + H2O
?
beta-chloro-L-Ala + H2O
?
beta-chloroalanine + H2O
?
beta-chloroalanine + H2O
pyruvate + NH4+ + Cl-
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-
-
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?
cysteine sulfinic acid + H2O
?
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?
D-serine
pyruvate + NH3
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with high diammonium hydrogen phosphate concentration, e.g. 1.2 M
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?
D-serine + indole
L-tryptophan + H2O
D-Trp + H2O
indole + pyruvate + NH4+
indole + L-Ser
L-Trp + ?
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-
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?
indole + pyruvate + NH4+
L-Trp + H2O
indole + S-methyl-L-Cys
L-Trp + ?
L-Ser + H2O
pyruvate + H2O
-
-
-
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?
L-serine + indole
L-tryptophan + H2O
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-
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?
L-Trp + H2O
indole + pyruvate + NH3
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effects of temperature and hydrostatic pressure on the equilibria and rate constants for quinoid intermediate formation from L-Trp and L-Met with H463 mutant enzyme
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?
L-Trp + H2O
indole + pyruvate + NH4+
L-Trp + H2O
pyruvate + NH3 + indole
L-tryptophan + H2O
indole + pyruvate + NH3
O-benzylserine + H2O
?
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?
O-methylserine + H2O
?
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?
oxindolyl-L-alanine + H2O
?
OIA, transition state analogue, the reaction of enzyme TIL mutant Y72F with OIA is accompanied by the appearance of intense absorption at 509 nm which may be explained by the formation of a quinonoid intermediate, transformation of the external aldimine into the quinonoid intermediate implies the transfer of alpha-proton to the base-acceptor in the active site. Oxindolyl-L-alanine also inhibits the enzyme
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?
S-(2-nitrophenyl)-L-cysteine + H2O
2-nitrobenzenethiolate + pyruvate + NH3
S-(2-nitrophenyl)-L-cysteine + H2O
?
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r
S-(o-nitrophenyl)-L-cysteine
?
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?
S-benzyl-L-Cys + H2O
phenylmethanethiol + pyruvate + NH4+
S-benzyl-L-cysteine + H2O
phenylmethanethiol + pyruvate + NH3
S-benzylcysteine + H2O
pyruvate + NH4+ + phenylmethanethiol
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-
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?
S-ethyl-L-Cys + H2O
ethanethiol + pyruvate + NH4+
S-ethyl-L-cysteine + H2O
?
S-ethyl-L-cysteine + H2O
ethanethiol + pyruvate + NH3
S-ethyl-L-cysteine + H2O
ethanethiol + pyruvate + NH4+
S-ethyl-L-cysteine + H2O
pyruvate + NH4+ + ethanethiol
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?
S-ethylcysteine + H2O
?
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?
S-methyl-L-Cys + H2O
methanethiol + pyruvate + NH4+
S-methyl-L-Cys + H2O
pyruvate + NH4+ + methanethiol
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?
S-methyl-L-Cys + indole
Trp + ?
S-methyl-L-cysteine
?
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?
S-methyl-L-cysteine + H2O
?
S-methyl-L-cysteine + H2O
methanethiol + pyruvate + NH3
S-methyl-L-cysteine + H2O
methanethiol + pyruvate + NH4+
S-o-nitrophenyl-L-Cys + H2O
o-nitrothiophenol + pyruvate + NH3
S-o-nitrophenyl-L-Cys + indole
Trp + ?
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reaction readily proceeds in water, it becomes impossible in water-organic solvents
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?
S-o-nitrophenyl-L-cysteine + H2O
o-nitrothiophenol + pyruvate + NH4+
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?
additional information
?
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5-hydroxy-L-Trp + H2O
?
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6% of the activity with L-Trp
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?
5-hydroxy-L-Trp + H2O
?
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14.3% of the activity with L-Trp
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?
5-hydroxy-L-Trp + H2O
?
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6.7% of the activity with L-Trp
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?
5-hydroxy-L-Trp + H2O
?
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6.7% of the activity with L-Trp
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?
5-methyl-L-Trp + H2O
?
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22% of the activity with L-Trp
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?
5-methyl-L-Trp + H2O
?
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21.1% of the activity with L-Trp
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?
5-methyl-L-Trp + H2O
?
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15.2% of the activity with L-Trp
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?
5-methyl-L-Trp + H2O
?
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15.2% of the activity with L-Trp
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?
beta-(benzimidazol-1-yl)-L-alanine + H2O
?
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reaction via aldimine intermediate, high activity with wild-type enzyme and mutant H463F
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?
beta-(benzimidazol-1-yl)-L-alanine + H2O
?
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reaction via aldimine intermediate, high activity with wild-type enzyme and mutant H463F
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?
beta-chloro-L-Ala + H2O
?
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?
beta-chloro-L-Ala + H2O
?
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?
beta-chloro-L-Ala + H2O
?
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?
beta-chloroalanine + H2O
?
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?
beta-chloroalanine + H2O
?
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?
Cys + H2O
?
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?
Cys + H2O
?
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36.4% of the activity with L-Trp
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?
Cys + H2O
?
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L-Cys
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?
Cys + H2O
?
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L-Cys
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?
Cys + H2O
?
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18.9% of the activity with L-Trp
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?
Cys + H2O
?
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L-Cys
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?
Cys + H2O
?
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18.9% of the activity with L-Trp
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?
Cys + H2O
?
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L-Cys
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?
Cys + indole
Trp + ?
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?
Cys + indole
Trp + ?
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?
Cys + indole
Trp + ?
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?
D-serine + indole
L-tryptophan + H2O
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the presence of 20% saturation concentration of diammonium hydrogen phosphate is required for this reaction
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?
D-serine + indole
L-tryptophan + H2O
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with high diammonium hydrogen phosphate concentration, e.g. 1.2 M
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?
D-Trp + H2O
indole + pyruvate + NH4+
in the presence of high concentrations of ammonium phosphate
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?
D-Trp + H2O
indole + pyruvate + NH4+
in the presence of high concentrations of ammonium phosphate
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?
indole + L-Cys
L-Trp + ?
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-
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?
indole + L-Cys
L-Trp + ?
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beta-replacement reaction
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?
indole + L-Cys
L-Trp + ?
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beta-replacement reaction
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?
indole + pyruvate + NH4+
L-Trp + H2O
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?
indole + pyruvate + NH4+
L-Trp + H2O
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?
indole + pyruvate + NH4+
L-Trp + H2O
-
-
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?
indole + pyruvate + NH4+
L-Trp + H2O
-
-
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?
indole + S-methyl-L-Cys
L-Trp + ?
-
-
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?
indole + S-methyl-L-Cys
L-Trp + ?
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beta-replacement reaction
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?
indole + S-methyl-L-Cys
L-Trp + ?
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beta-replacement reaction
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
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?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
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?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
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?
L-Trp + H2O
indole + pyruvate + NH4+
Escherichia aurescens
-
-
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?
L-Trp + H2O
indole + pyruvate + NH4+
Escherichia aurescens
-
-
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?
L-Trp + H2O
indole + pyruvate + NH4+
Escherichia aurescens
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-
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?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
-
r
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
r
L-Trp + H2O
indole + pyruvate + NH4+
-
the product indole is involved in cell signaling, involved in cell cycle regulation
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-
r
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
r
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
Paracolobactrum coliforme
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
Paracolobactrum sp.
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
4.1.99.1 tryptophanase
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