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4.1.99.1: tryptophanase

This is an abbreviated version!
For detailed information about tryptophanase, go to the full flat file.

Word Map on EC 4.1.99.1

Reaction

L-tryptophan
+
H2O
=
indole
+
pyruvate
+
NH3

Synonyms

L-tryptophan indole-lyase, L-tryptophanase, TIL, tna2, TnaA, tnaA2, TNase, Tpase, Trpase, tryptophan indole lyase, tryptophan indole-lyase, tryptophan-indole lyase, tryptophanase, tryptophanase 2, VcTrpase

ECTree

     4 Lyases
         4.1 Carbon-carbon lyases
             4.1.99 Other carbon-carbon lyases
                4.1.99.1 tryptophanase

Substrates Products

Substrates Products on EC 4.1.99.1 - tryptophanase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2-oxindolyl-L-alanine + H2O
?
show the reaction diagram
-
-
-
?
4-methyl-Trp + H2O
?
show the reaction diagram
-
52% of the activity with L-Trp
-
-
?
5-hydroxy-L-Trp + H2O
?
show the reaction diagram
5-hydroxyindole + L-Cys
5-hydroxy-L-Trp + ?
show the reaction diagram
-
-
-
-
?
5-hydroxyindole + S-methyl-L-Cys
5-hydroxy-L-Trp + ?
show the reaction diagram
-
-
-
-
?
5-methyl-L-Trp + H2O
?
show the reaction diagram
5-methylindole + L-Cys
5-methyl-L-Trp + ?
show the reaction diagram
-
-
-
-
?
5-methylindole + S-methyl-L-Cys
5-methyl-L-Trp + ?
show the reaction diagram
-
-
-
-
?
6-methyl-Trp + H2O
?
show the reaction diagram
-
44% of the activity with L-Trp
-
-
?
alpha,beta-diaminopropionic acid
?
show the reaction diagram
-
-
-
-
?
beta-(benzimidazol-1-yl)-L-alanine + H2O
?
show the reaction diagram
beta-chloro-L-Ala + H2O
?
show the reaction diagram
beta-chloroalanine + H2O
?
show the reaction diagram
beta-chloroalanine + H2O
pyruvate + NH4+ + Cl-
show the reaction diagram
-
-
-
-
?
Cys + H2O
?
show the reaction diagram
Cys + indole
Trp + ?
show the reaction diagram
cysteine sulfinic acid + H2O
?
show the reaction diagram
-
-
-
-
?
D-serine
pyruvate + NH3
show the reaction diagram
-
with high diammonium hydrogen phosphate concentration, e.g. 1.2 M
-
-
?
D-serine + indole
L-tryptophan + H2O
show the reaction diagram
D-Trp + H2O
indole + pyruvate + NH4+
show the reaction diagram
indole + L-Cys
L-Trp + ?
show the reaction diagram
indole + L-Ser
L-Trp + ?
show the reaction diagram
-
-
-
?
indole + pyruvate + NH4+
L-Trp + H2O
show the reaction diagram
indole + S-methyl-L-Cys
L-Trp + ?
show the reaction diagram
L-Ser + H2O
pyruvate + H2O
show the reaction diagram
-
-
-
-
?
L-serine + indole
L-tryptophan + H2O
show the reaction diagram
-
-
-
-
?
L-Trp + H2O
indole + pyruvate + NH3
show the reaction diagram
-
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
-
-
?
L-Trp + H2O
indole + pyruvate + NH4+
show the reaction diagram
L-Trp + H2O
pyruvate + NH3 + indole
show the reaction diagram
L-tryptophan + H2O
indole + pyruvate + NH3
show the reaction diagram
O-benzylserine + H2O
?
show the reaction diagram
-
-
-
-
?
O-methylserine + H2O
?
show the reaction diagram
-
-
-
-
?
oxindolyl-L-alanine + H2O
?
show the reaction diagram
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
-
-
?
S-(2-nitrophenyl)-L-cysteine + H2O
2-nitrobenzenethiolate + pyruvate + NH3
show the reaction diagram
S-(2-nitrophenyl)-L-cysteine + H2O
?
show the reaction diagram
-
-
-
-
r
S-(o-nitrophenyl)-L-cysteine
?
show the reaction diagram
-
-
-
?
S-benzyl-L-Cys + H2O
phenylmethanethiol + pyruvate + NH4+
show the reaction diagram
S-benzyl-L-cysteine + H2O
phenylmethanethiol + pyruvate + NH3
show the reaction diagram
S-benzylcysteine + H2O
?
show the reaction diagram
S-benzylcysteine + H2O
pyruvate + NH4+ + phenylmethanethiol
show the reaction diagram
-
-
-
-
?
S-ethyl-L-Cys + H2O
ethanethiol + pyruvate + NH4+
show the reaction diagram
S-ethyl-L-cysteine + H2O
?
show the reaction diagram
S-ethyl-L-cysteine + H2O
ethanethiol + pyruvate + NH3
show the reaction diagram
S-ethyl-L-cysteine + H2O
ethanethiol + pyruvate + NH4+
show the reaction diagram
S-ethyl-L-cysteine + H2O
pyruvate + NH4+ + ethanethiol
show the reaction diagram
-
-
-
-
?
S-ethylcysteine + H2O
?
show the reaction diagram
-
-
-
-
?
S-methyl-L-Cys + H2O
?
show the reaction diagram
S-methyl-L-Cys + H2O
methanethiol + pyruvate + NH4+
show the reaction diagram
S-methyl-L-Cys + H2O
pyruvate + NH4+ + methanethiol
show the reaction diagram
-
-
-
-
?
S-methyl-L-Cys + indole
Trp + ?
show the reaction diagram
S-methyl-L-cysteine
?
show the reaction diagram
-
-
-
?
S-methyl-L-cysteine + H2O
?
show the reaction diagram
S-methyl-L-cysteine + H2O
methanethiol + pyruvate + NH3
show the reaction diagram
S-methyl-L-cysteine + H2O
methanethiol + pyruvate + NH4+
show the reaction diagram
S-o-nitrophenyl-L-Cys + H2O
o-nitrothiophenol + pyruvate + NH3
show the reaction diagram
S-o-nitrophenyl-L-Cys + indole
Trp + ?
show the reaction diagram
-
reaction readily proceeds in water, it becomes impossible in water-organic solvents
-
?
S-o-nitrophenyl-L-cysteine + H2O
o-nitrothiophenol + pyruvate + NH4+
show the reaction diagram
-
-
-
-
?
Ser + H2O
?
show the reaction diagram
Ser + indole
Trp + ?
show the reaction diagram
Ser + indole
Trp + H2O
show the reaction diagram
additional information
?
-