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L-tyrosine + H2O = phenol + pyruvate + NH3
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism
-
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism
-
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism
-
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism
L-tyrosine + H2O = phenol + pyruvate + NH3
single-base racemization mechanism, proceeds with retention of configuration at C-beta
-
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism appears to require two bases, one of which abstracts the proton from the 2-position of the substrate to form a quinonoid intermediate and the second of which acting in concert with proton transfer from the first group to C-1 of the phenolic ring, abstracts the substrate hydroxyl group to facilitate cyclohexadienone formation and subsequent elimination of phenol
-
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism appears to require two bases, one of which abstracts the proton from the 2-position of the substrate to form a quinonoid intermediate and the second of which acting in concert with proton transfer from the first group to C-1 of the phenolic ring, abstracts the substrate hydroxyl group to facilitate cyclohexadienone formation and subsequent elimination of phenol
-
L-tyrosine + H2O = phenol + pyruvate + NH3
NH3 is the first substrate which interacts with bound pyridoxal 5'-phosphate, pyruvate is the second substrate
-
L-tyrosine + H2O = phenol + pyruvate + NH3
reversible cleavage of the Cbeta-Cgamma bond of L-tyrosine in the final stage of the beta-elimination, via intermediates: internal aldimine, external aldimine, quinoid, ketoquinoid, alpha-aminoacrylate, and internal aldimine, stepwise mechanism, overview
-
L-tyrosine + H2O = phenol + 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 TPL show rapid formation of external aldimine intermediate, followed by deprotonation to give a quinonoid intermediate absorbing at about 500 nm. The mechanism of TPL requires both substrate strain and acid/base catalysis, and substrate strain is probably responsible for the very high substrate specificity of TPL. Acid-base catalysis mechanism of TPL, overview
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism of alpha,beta-elimination of L-tyrosine catalyzed by enzyme TPL
L-tyrosine + H2O = phenol + pyruvate + NH3
mechanism of alpha,beta-elimination of L-tyrosine catalyzed by enzyme TPL, detailed overview
L-tyrosine + H2O = phenol + pyruvate + NH3
-
-
-
-
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1-amino-2-(4-hydroxyphenyl)-ethyl phosphinic acid + H2O
phenol + ?
-
-
-
?
2,5-difluorotyrosine + H2O
2,5-difluorophenol + pyruvate + NH3
-
-
-
?
2,6-difluorotyrosine + H2O
2,6-difluorophenol + pyruvate + NH3
-
-
-
?
2-bromo-L-Tyr + H2O
2-bromophenol + pyruvate + NH3
-
-
-
r
2-bromophenol + pyruvate + NH3
2-bromo-L-Tyr + H2O
-
-
-
r
2-chloro-L-Tyr + H2O
2-chlorophenol + pyruvate + NH3
2-chlorophenol + pyruvate + NH3
2-chloro-L-Tyr + H2O
-
-
-
r
2-fluoro-L-Tyr + H2O
2-fluorophenol + pyruvate + NH3
2-fluorophenol + pyruvate + NH3
2-fluoro-L-Tyr + H2O
-
-
-
r
2-fluorotyrosine + H2O
2-fluorophenol + pyruvate + NH3
-
-
-
?
2-methoxy-L-Tyr + H2O
2-methoxyphenol + pyruvate + NH3
-
-
-
r
2-methoxyphenol + pyruvate + NH3
2-methoxy-L-Tyr + H2O
-
-
-
r
2-methyl-L-Tyr + H2O
2-methylphenol + pyruvate + NH3
-
-
-
r
2-methylphenol + pyruvate + NH3
2-methyl-L-Tyr + H2O
-
-
-
r
3,4-dihydroxyphenyl-L-Ala + H2O
pyrocatechol + NH3 + pyruvate
3,4-dihydroxyphenyl-L-alanine
?
Symbiobacterium sp.
-
-
-
?
3,4-dihydroxyphenyl-L-alanine + H2O
pyrocatechol + NH3 + pyruvate
-
-
-
-
?
3,5-difluorotyrosine + H2O
3,5-difluorophenol + pyruvate + NH3
-
-
-
?
3-bromo-L-Tyr + H2O
3-bromophenol + pyruvate + NH3
-
-
-
r
3-bromo-L-tyrosine + H2O
3-bromophenol + pyruvate + NH3
-
-
-
-
?
3-bromophenol + pyruvate + NH3
3-bromo-L-Tyr + H2O
-
-
-
r
3-chloro-L-Tyr + H2O
3-chlorophenol + pyruvate + NH3
-
-
-
r
3-chloro-L-tyrosine + H2O
3-chlorophenol + pyruvate + NH3
-
-
-
-
?
3-chloro-L-tyrosine + H2O
?
-
substrate of mutant M379V, not of the wild-type enzyme
-
-
?
3-chlorophenol + pyruvate + NH3
3-chloro-L-Tyr + H2O
-
-
-
r
3-chlorotyrosine + H2O
3-chlorophenol + pyruvate + NH3
-
-
-
?
3-fluoro-L-Tyr + H2O
3-fluorophenol + pyruvate + NH3
3-fluoro-L-tyrosine
3-fluorophenol + pyruvate + NH3
-
-
-
?
3-fluoro-L-tyrosine + H2O
3-fluoro-phenol + pyruvate + NH3
-
-
?
3-fluoro-L-tyrosine + H2O
3-fluorophenol + pyruvate + NH3
3-fluoro-L-tyrosine + H2O
?
-
substrate of mutant M379V, not of the wild-type enzyme
-
-
?
3-fluorophenol + pyruvate + NH3
3-fluoro-L-Tyr + H2O
-
-
-
r
3-fluorotyrosine + H2O
3-fluorophenol + pyruvate + NH3
-
-
-
?
3-iodo-L-tyrosine + H2O
3-iodophenol + pyruvate + NH3
-
-
-
-
?
3-methoxy-L-tyrosine + H2O
?
-
substrate of mutant M379V, not of the wild-type enzyme
-
-
?
3-methyl-L-Tyr + H2O
3-methylphenol + pyruvate + NH3
-
-
-
r
3-methyl-L-tyrosine + H2O
?
-
substrate of mutant M379V, not of the wild-type enzyme
-
-
?
3-methylphenol + pyruvate + NH3
3-methyl-L-Tyr + H2O
-
-
-
r
allothreonine + ?
Gly + ?
-
-
-
?
beta-chloro-L-alanine + H2O
?
beta-chloro-L-alanine + H2O
Cl- + pyruvate + NH3
-
-
-
r
catechol + pyruvate
L-DOPA + H2O
catechol + pyruvate + NH3
3,4-dihydroxyphenyl-L-alanine
catechol + pyruvate + NH3
L-dihydroxyphenylalanine
catechol + pyruvic acid
L-dopa + H2O
-
-
-
-
?
D-serine + H2O
?
Symbiobacterium sp.
-
at 11% the rate of L-tyrosine
-
?
D-tyrosine + H2O
phenol + pyruvate + NH3
L-3-4 dihydroxyphenylalanine + H2O
catechol + pyruvate + NH3
L-Ala + pyridoxal phosphate
pyridoxamine phosphate + keto acid
-
-
-
-
ir
L-alanine + H2O
?
-
wild-type enzyme forms the Ala quinonoid intermediate when incubated with L-Ala
-
-
?
L-Asp + H2O
formate + pyruvate + NH3
L-asparagine + H2O
?
-
-
-
-
?
L-Cys + H2O
? + pyruvate + NH3
L-cysteine + H2O
thiophenol + pyruvate + NH3
12% of the activity with L-tyrosine
-
-
r
L-cystine + H2O
? + pyruvate + NH3
L-DOPA + H2O
pyrocatechol + pyruvate + NH4+
42% of the activity with L-tyrosine
-
-
r
L-m-Tyr + pyridoxal phosphate
pyridoxamine phosphate + keto acid
-
-
-
-
ir
L-methionine + H2O
?
-
-
-
-
?
L-Phe + pyridoxal phosphate
pyridoxamine phosphate + keto acid
-
-
-
-
ir
L-phenylalanine + H2O
?
-
low activity
-
-
?
L-phenylalanine + H2O
? + pyruvate + NH3
7% of the activity with L-tyrosine
-
-
r
L-Ser + phenol
L-Tyr + H2O
L-Ser + pyridoxal phosphate
pyridoxamine phosphate + keto acid
-
-
-
-
ir
L-Ser + pyrocatechol
3,4-dihydroxyphenyl-L-Ala + H2O
L-serine + H2O
?
Symbiobacterium sp.
-
-
-
?
L-serine + H2O
pyruvate + NH3
9% of the activity with L-tyrosine
-
-
r
L-tryptophan + H2O
indole + pyruvate + NH3
L-Tyr + H2O
phenol + pyruvate + NH3
-
-
-
-
?
L-tyrosine + H2O
3,4-dihydroxyphenyl-L-alanine
L-tyrosine + H2O
phenol + pyruvate + NH3
L-valine + H2O
?
-
-
-
-
?
L-valine + H2O
? + pyruvate + NH3
6% of the activity with L-tyrosine
-
-
r
O-benzyl-L-Cys + H2O
?
-
-
-
?
O-benzyl-L-Ser + H2O
?
-
-
-
?
o-chlorophenol + H2O
?
-
substrate of mutant M379V, not of the wild-type enzyme
-
-
?
o-cresol + H2O
?
-
substrate of mutant M379V, not of the wild-type enzyme
-
-
?
o-methoxyphenol + H2O
?
-
substrate of mutant M379V, not of the wild-type enzyme
-
-
?
phenol + pyruvate + NH3
L-tyrosine + H2O
-
-
-
r
phenol + pyruvate + NH3
Tyr + H2O
pyrocatechol + pyruvate + NH3
3,4-dihydroxyphenyl-L-Ala + H2O
pyrocatechol + pyruvate + NH4+
L-DOPA + H2O
resorcinol + pyruvate + NH3
2,4-dihydroxyphenyl-L-Ala
-
-
-
?
S-(2-nitrophenyl)-L-cysteine
?
-
-
-
-
?
S-(2-nitrophenyl)-L-cysteine + H2O
2-nitrobenzenethiolate + pyruvate + NH3
S-(o-nitrophenyl)-L-Cys + H2O
?
-
-
-
-
?
S-(o-nitrophenyl)-L-Cys + H2O
? + pyruvate + NH3
-
-
-
-
?
S-(o-nitrophenyl)-L-cysteine
?
S-(o-nitrophenyl)-L-cysteine + H2O
?
S-benzoyl-L-Cys + H2O
?
-
-
-
-
?
S-benzyl-L-Cys + H2O
? + pyruvate + NH3
S-benzyl-L-cysteine
? + pyruvate + NH3
-
-
-
-
?
S-benzyl-L-cysteine + H2O
thiophenol + pyruvate + NH3
-
-
-
r
S-ethyl-L-cysteine
? + pyruvate + NH3
-
-
-
-
?
S-ethyl-L-cysteine + H2O
?
-
-
-
?
S-ethyl-L-cysteine + H2O
ethanethiol + pyruvate + NH3
-
-
-
r
S-methyl-L-Cys + H2O
? + pyruvate + NH3
S-methyl-L-cysteine
? + pyruvate + NH3
-
-
-
-
?
S-methyl-L-cysteine + H2O
?
Symbiobacterium sp.
-
385% of activity compared to L-tyrosine
-
?
S-methyl-L-cysteine + H2O
methanethiol + pyruvate + NH3
-
-
-
r
S-methyl-L-cysteine + H2O
methanthiol + pyruvate + NH3
13% of the activity with L-tyrosine
-
-
r
S-o-nitrophenyl-L-cysteine + H2O
?
-
-
-
-
?
Ser + H2O
? + pyruvate + NH3
Thr + ?
2-oxobutanoate + ?
Tyr + H2O
phenol + pyruvate + NH3
additional information
?
-
2-chloro-L-Tyr + H2O
2-chlorophenol + pyruvate + NH3
-
-
-
r
2-chloro-L-Tyr + H2O
2-chlorophenol + pyruvate + NH3
-
-
-
-
?
2-fluoro-L-Tyr + H2O
2-fluorophenol + pyruvate + NH3
-
-
-
r
2-fluoro-L-Tyr + H2O
2-fluorophenol + pyruvate + NH3
-
-
-
-
?
3,4-dihydroxyphenyl-L-Ala + H2O
pyrocatechol + NH3 + pyruvate
-
-
-
?
3,4-dihydroxyphenyl-L-Ala + H2O
pyrocatechol + NH3 + pyruvate
-
-
-
-
?
3,4-dihydroxyphenyl-L-Ala + H2O
pyrocatechol + NH3 + pyruvate
-
i.e. L-dopa
-
?
3,4-dihydroxyphenyl-L-Ala + H2O
pyrocatechol + NH3 + pyruvate
-
i.e. L-dopa
-
?
3-chloro-L-Ala + H2O
?
-
-
-
-
?
3-chloro-L-Ala + H2O
?
-
-
-
-
?
3-chloro-L-Ala + H2O
?
-
-
-
-
?
3-chloro-L-Ala + H2O
?
-
-
-
-
?
3-fluoro-L-Tyr + H2O
3-fluorophenol + pyruvate + NH3
-
-
-
r
3-fluoro-L-Tyr + H2O
3-fluorophenol + pyruvate + NH3
-
-
-
-
?
3-fluoro-L-Tyr + H2O
3-fluorophenol + pyruvate + NH3
-
-
-
-
?
3-fluoro-L-tyrosine + H2O
3-fluorophenol + pyruvate + NH3
-
-
-
-
?
3-fluoro-L-tyrosine + H2O
3-fluorophenol + pyruvate + NH3
-
-
-
r
3-fluoro-L-tyrosine + H2O
3-fluorophenol + pyruvate + NH3
3-fluoro-L-tyrosine also is a good substrate for the wild-type enzyme
-
-
r
Ala + H2O
?
-
L-Ala
-
-
?
Ala + H2O
?
-
D-Ala
-
-
?
beta-chloro-L-alanine
?
-
-
-
?
beta-chloro-L-alanine
?
-
-
?
beta-chloro-L-alanine + H2O
?
-
-
-
r
beta-chloro-L-alanine + H2O
?
Symbiobacterium sp.
-
500% of activity compared to L-tyrosine
-
?
beta-chloro-L-alanine + H2O
?
-
500% of activity compared to L-tyrosine
-
?
catechol + pyruvate
L-DOPA + H2O
-
-
-
r
catechol + pyruvate
L-DOPA + H2O
-
-
-
r
catechol + pyruvate + NH3
3,4-dihydroxyphenyl-L-alanine
-
TPL is well-correlated to cytoplasmic 3,4-dihydroxyphenyl-L-alanine levels
-
-
r
catechol + pyruvate + NH3
3,4-dihydroxyphenyl-L-alanine
-
TPL is well-correlated to cytoplasmic 3,4-dihydroxyphenyl-L-alanine levels
-
-
r
catechol + pyruvate + NH3
3,4-dihydroxyphenyl-L-alanine
-
-
-
-
r
catechol + pyruvate + NH3
L-dihydroxyphenylalanine
-
-
-
?
catechol + pyruvate + NH3
L-dihydroxyphenylalanine
-
-
-
-
?
D-tyrosine + H2O
phenol + pyruvate + NH3
Symbiobacterium sp.
-
at 7% the rate of L-tyrosine
-
?
D-tyrosine + H2O
phenol + pyruvate + NH3
-
at 7% the rate of L-tyrosine
-
?
L-2-aminoadipate + H2O
?
-
no activity with wild-type enzyme, activity with mutant enzyme R100T/V283R
-
-
?
L-2-aminoadipate + H2O
?
-
no activity with wild-type enzyme, activity with mutant enzyme R100T/V283R
-
-
?
L-3-4 dihydroxyphenylalanine + H2O
catechol + pyruvate + NH3
-
L-dopa
-
-
r
L-3-4 dihydroxyphenylalanine + H2O
catechol + pyruvate + NH3
-
L-DOPA, alpha-beta elimination
-
-
r
L-3-4 dihydroxyphenylalanine + H2O
catechol + pyruvate + NH3
-
L-dopa
-
-
r
L-Asp + H2O
formate + pyruvate + NH3
-
no activity with wild-type enzyme, activity with mutant enzyme R100T/V283R
-
?
L-Asp + H2O
formate + pyruvate + NH3
-
no activity with wild-type enzyme, activity with mutant enzyme R100T/V283R
-
?
L-Cys + H2O
? + pyruvate + NH3
-
-
-
?
L-Cys + H2O
? + pyruvate + NH3
-
-
-
?
L-Cys + H2O
? + pyruvate + NH3
-
-
-
?
L-Cys + H2O
? + pyruvate + NH3
-
-
-
-
?
L-cysteine + H2O
?
Symbiobacterium sp.
-
-
-
?
L-cysteine + H2O
?
-
-
-
?
L-cystine + H2O
? + pyruvate + NH3
-
-
-
?
L-cystine + H2O
? + pyruvate + NH3
-
-
-
?
L-Glu + H2O
?
-
no activity with wild-type enzyme, activity with mutant enzyme R100T/V283R
-
-
?
L-Glu + H2O
?
-
no activity with wild-type enzyme, activity with mutant enzyme R100T/V283R
-
-
?
L-Phe + H2O
?
-
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
Pseudomonas pelurida
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
Pseudomonas trifolii
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + phenol
L-Tyr + H2O
-
-
-
?
L-Ser + pyrocatechol
3,4-dihydroxyphenyl-L-Ala + H2O
-
-
-
?
L-Ser + pyrocatechol
3,4-dihydroxyphenyl-L-Ala + H2O
-
-
-
?
L-Ser + pyrocatechol
3,4-dihydroxyphenyl-L-Ala + H2O
-
-
-
?
L-Ser + pyrocatechol
3,4-dihydroxyphenyl-L-Ala + H2O
-
-
-
?
L-Ser + pyrocatechol
3,4-dihydroxyphenyl-L-Ala + H2O
-
-
-
?
L-Ser + pyrocatechol
3,4-dihydroxyphenyl-L-Ala + H2O
4.1.99.2 tyrosine phenol-lyase
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