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(1,1'-biphenyl)acrylic acid + NH3
([1,1'-biphenyl]-4-yl)alanine
-
no product is detected with wild-type enzyme or either single mutants, 8% conversion with mutant enzyme F137A/I460V after 20 h
-
-
?
(2'-chloro-5-phenylthiophen-2-yl)acrylic acid + NH3
(2'-chloro-5-phenylthiophen-2-yl)alanine
-
no product is detected with wild-type enzyme or either single mutants, 2% conversion with mutant enzyme F137A/I460V after 20 h
-
-
?
(2'-chloro-5-phenylthiophen-2-yl)alanine
(2'-chloro-5-phenylthiophen-2-yl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion
-
-
?
(2-phenylthiazol-4-yl)alanine
(2-phenylthiazol-4-yl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutant F137A provides low high conversion
-
-
?
(2E)-3-(1-benzofuran-2-yl)acrylic acid + NH3
2-amino-3-(1-benzofuran-2-yl)propanoic acid
-
-
-
-
r
(2E)-3-(1-benzothien-2-yl)acrylic acid + NH3
2-amino-3-(1-benzothien-2-yl)propanoic acid
-
-
-
-
r
(2E)-3-(2-furyl)acrylic acid + NH3
(S)-2-amino-3-(2-furyl)propanoic acid
-
-
-
-
r
(2E)-3-(2-thienyl)acrylic acid + NH3
2-amino-3-(2-thienyl)propanoic acid
-
-
-
-
r
(2E)-3-bromo-cinnamic acid + NH3
3-bromo-L-phenylalanine
112% compared to activity with trans-cinnamate
-
-
?
(2E)-3-fluoro-cinnamic acid + NH3
3-fluoro-L-phenylalanine
128% compared to activity with trans-cinnamate
-
-
?
(2E)-3-nitro-cinnamic acid + NH3
4-nitro-L-phenylalanine
54% compared to activity with trans-cinnamate
-
-
?
(2E)-4-amino-cinnamic acid + NH3
4-amino-L-phenylalanine
-
poor substrate
-
-
r
(2E)-4-bromo-cinnamic acid + NH3
4-bromo-L-phenylalanine
17% compared to activity with trans-cinnamate
-
-
?
(2E)-4-fluoro-cinnamic acid + NH3
4-fluoro-L-phenylalanine
(2E)-4-formyl-cinnamic acid + NH3
4-formyl-L-phenylalanine
-
-
-
-
r
(2E)-4-hydroxycinnamate + NH3
L-tyrosine
-
-
-
-
r
(2E)-4-methyl-cinnamic acid + NH3
4-methyl-L-phenylalanine
-
-
-
-
r
(2E)-4-nitro-cinnamic acid + NH3
4-nitro-L-phenylalanine
-
-
-
-
r
(2E)-4-trifluoromethyl-cinnamic acid + NH3
4-trifluoromethyl-L-phenylalanine
-
poor substrate
-
-
r
(2S)-2-amino-3-(3-fluorophenyl)propanoic acid
(2E)-3-(3-fluorophenyl)prop-2-enoic acid + NH3
-
-
-
r
(2S)-2-amino-3-(3-hydroxyphenyl)propanoic acid
(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid + NH3
-
-
-
r
(2S)-2-amino-3-(4-fluorophenyl)propanoic acid
(2E)-3-(4-fluorophenyl)prop-2-enoic acid + NH3
-
-
-
r
(2S)-2-amino-3-(4-nitrophenyl)propanoic acid
(2E)-3-(4-nitrophenyl)prop-2-enoic acid + NH3
-
-
-
r
(2S)-2-amino-3-(pyridin-3-yl)propanoic acid
(2E)-3-(pyridin-3-yl)prop-2-enoic acid + NH3
-
-
-
r
(2S)-2-amino-3-(pyridin-4-yl)propanoic acid
(2E)-3-(pyridin-4-yl)prop-2-enoic acid + NH3
-
-
-
r
(2S)-2-amino-3-phenylpropanoic acid
(2E)-3-phenylprop-2-enoic acid + NH3
-
-
-
r
(2S)-2-amino-3-[4-(trifluoromethyl)phenyl]propanoic acid
(2E)-3-[4-(trifluoromethyl)phenyl]prop-2-enoic acid + NH3
-
-
-
r
(3-methoxy)alanine
(3-methoxy)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion
-
-
?
(4'-chloro-5-phenylthiophen-2-yl)alanine
(4'-chloro-5-phenylthiophen-2-yl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion
-
-
?
(4'-fluoro-[1,1'-biphenyl]-4-yl)acrylic acid + NH3
(4'-fluoro-[1,1'-biphenyl]-4-yl)alanine
-
no product is detected with wild-type enzyme or either single mutants, 6% conversion with mutant enzyme F137A/I460V after 20 h
-
-
?
(4'-fluoro-[1,1'-biphenyl]-4-yl)alanine
(4'-fluoro-[1,1'-biphenyl]-4-yl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion. 39% conversion with with mutant enzyme F137A/I460V, 18% conversion with mutant enzyme F137A/L138V, 15% conversion with mutant enzyme F137A
-
-
?
(5-phenylthiophen-2-yl)acrylic acid + NH3
(5-phenylthiophen-2-yl)alanine
-
no product is detected with wild-type enzyme or either single mutants, 6% conversion with mutant enzyme F137A/I460V after 20 h
-
-
?
(5-phenylthiophen-2-yl)alanine
(5-phenylthiophen-2-yl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion. 48% conversion with mutant enzyme F137A/L138V, 44% conversion with mutant enzyme F137
-
-
?
(E)-cinnamate + NH3
L-phenylalanine
-
-
-
-
r
(E)-pent-2-ene-4-ynoate + NH3
L-propargylglycine
-
-
-
-
r
(naphthalen-2-yl)alanine
(naphthalen-2-yl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion
-
-
?
(styryl)acrylic acid + NH3
(styryl)alanine
-
no product is detected with wild-type enzyme or either single mutants, but 22% and 27%, respectively, conversion can be achieved with the F137V/I460V and F137V/I460A double mutants
-
-
?
(styryl)alanine
(styryl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion
-
-
?
([1,1'-biphenyl]-4-yl)alanine
(1,1'-biphenyl)acrylic acid + NH3
-
wild-type enzyme shows a very poor conversion even after long reaction times up to 48 h, mutants I460V and F137V and F137A provide medium to high conversion
-
-
?
2,3,4,5,6-pentafluoro-L-phenylalanine
2,3,4,5,6-pentafluoro-trans-cinnamate + NH3
-
-
-
r
2,6-difluoro-L-phenylalanine
2,6-difluoro-trans-cinnamate + NH3
-
-
-
r
2-amino-3-(1-benzofuran-2-yl)propanoic acid
(2E)-3-(1-benzofuran-2-yl)acrylic acid + NH3
-
49% of the rate with L-phenylalanine
-
-
r
2-amino-3-(1-benzothien-2-yl)propanoic acid
(2E)-3-(1-benzothien-2-yl)acrylic acid + NH3
-
14% of the rate with L-phenylalanine
-
-
r
2-amino-3-(2-furyl)propanoic acid
(2E)-3-(2-furyl)acrylic acid + NH3
-
34% of the rate with L-phenylalanine
-
-
r
2-amino-3-(2-thienyl)propanoic acid
(2E)-3-(2-thienyl)acrylic acid + NH3
-
101% of the rate with L-phenylalanine
-
-
r
2-amino-3-(3-thienyl)propanoic acid
(2E)-3-(3-thienyl)acrylic acid + NH3
-
16% of the rate with L-phenylalanine
-
-
r
2-chloro-L-phenylalanine
2-chloro-trans-cinnamate + NH3
-
-
-
r
2-chloro-trans-cinnamate + NH3
2-chloro-L-phenylalanine
2-fluoro-L-phenylalanine
2-fluoro-trans-cinnamate + NH3
-
-
-
r
2-fluoro-trans-cinnamate + NH3
2-fluoro-L-phenylalanine
2-hydroxy-trans-cinnamate + NH3
2-hydroxy-L-phenylalanine
2-methoxy-trans-cinnamate + NH3
2-methoxy-L-phenylalanine
3,4-dihydroxyphenylalanine
?
-
29% of the activity with L-Phe
-
-
?
3,5-difluoro-L-phenylalanine
3,5-difluoro-trans-cinnamate + NH3
-
-
-
r
3-chloro-L-phenylalanine
3-chloro-trans-cinnamate + NH3
3-chloro-trans-cinnamate + NH3
3-chloro-L-phenylalanine
3-fluoro-L-phenylalanine
3-fluoro-trans-cinnamate + NH3
-
-
-
r
3-fluoro-trans-cinnamate + NH3
3-fluoro-L-phenylalanine
3-hydroxy-trans-cinnamate + NH3
3-hydroxy-L-phenylalanine
3-methoxy-trans-cinnamate + NH3
3-methoxy-L-phenylalanine
4-chloro-L-phenylalanine
4-chloro-trans-cinnamate + NH3
-
-
-
?
4-chloro-trans-cinnamate + NH3
4-chloro-L-phenylalanine
4-fluoro-L-phenylalanine
4-fluoro-(E)-cinnamate + NH3
-
-
-
-
r
4-fluoro-L-phenylalanine
4-fluoro-trans-cinnamate + NH3
4-fluoro-trans-cinnamate + NH3
4-fluoro-L-phenylalanine
4-hydroxy-trans-cinnamate + NH3
4-hydroxy-L-phenylalanine
4-methoxy-trans-cinnamate + NH3
4-methoxy-L-phenylalanine
4-nitro-L-phenylalanine
4-nitro-(E)-cinnamate + NH3
-
-
-
-
r
4-nitro-trans-cinnamate + NH3
4-nitro-D-phenylalanine
-
-
-
?
4-nitro-trans-cinnamate + NH3
4-nitro-L-phenylalanine
-
-
-
?
4-trifluoromethyl-L-phenylalanine
4-trifluoromethyl-(E)-cinnamate + NH3
-
-
-
-
r
beta-(5-pyrimidinyl)-D,L-alanine
?
-
-
-
?
chlorophenylalanine
?
Streptomyces verticillatus
-
-
-
-
?
fluorophenylalanine
trans-(4-fluoro)cinnamate + NH3
L-Phe
(E)-cinnamate + NH3
L-phenylalanine
(E)-cinnamate + NH3
L-phenylalanine
trans-cinnamate + NH3
L-phenylalanine methyl ester
?
-
-
-
-
r
L-propargylglycine
(E)-pent-2-ene-4-ynoate + NH3
-
-
-
-
r
L-styrylalanine
(styryl)acrylic acid + NH3
-
-
-
-
?
L-Tyr
(2E)-4-hydroxycinnamate + NH3
L-Tyr
p-coumarate + NH3
-
-
-
?
L-tyrosine
(2E)-4-hydroxycinnamate + NH3
-
poor substrate
-
-
r
L-tyrosine
p-coumarate + NH3
L-tyrosine
trans-p-hydroxycinnamate + NH3
the enzyme is specific for L-phenylalanine, and shows low activity with L-tyrosine
-
-
?
N-methyl-L-phenylalanine
trans-cinnamate + methylamine
-
-
-
?
rac-(E)-2-amino-5-(4-chlorophenyl)pent-4-enoic acid
(2E,4E)-5-(4-chlorophenyl)penta-2,4-dienoic acid + NH3
-
-
-
-
?
rac-(E)-2-amino-5-phenylpent-4-enoic acid
(2E,4E)-5-phenylpenta-2,4-dienoic acid + NH3
-
-
-
-
?
trans-cinnamate + NH3
L-alpha-phenylalanine + L-beta-phenylalanine
-
-
-
r
trans-cinnamate + NH3
L-phenylalanine
trans-cinnamic acid + NH3
L-phenylalanine
additional information
?
-
(2E)-4-fluoro-cinnamic acid + NH3
4-fluoro-L-phenylalanine
-
-
-
-
r
(2E)-4-fluoro-cinnamic acid + NH3
4-fluoro-L-phenylalanine
109% compared to activity with trans-cinnamate
-
-
?
2-chloro-trans-cinnamate + NH3
2-chloro-L-phenylalanine
-
-
-
?
2-chloro-trans-cinnamate + NH3
2-chloro-L-phenylalanine
96.4% conversion
-
-
?
2-chloro-trans-cinnamate + NH3
2-chloro-L-phenylalanine
50.5% conversion
-
-
?
2-fluoro-trans-cinnamate + NH3
2-fluoro-L-phenylalanine
96.1% conversion
-
-
?
2-fluoro-trans-cinnamate + NH3
2-fluoro-L-phenylalanine
95.8% conversion
-
-
?
2-hydroxy-trans-cinnamate + NH3
2-hydroxy-L-phenylalanine
22.0% conversion
-
-
?
2-hydroxy-trans-cinnamate + NH3
2-hydroxy-L-phenylalanine
15.5% conversion
-
-
?
2-methoxy-trans-cinnamate + NH3
2-methoxy-L-phenylalanine
52.7% conversion
-
-
?
2-methoxy-trans-cinnamate + NH3
2-methoxy-L-phenylalanine
54.6% conversion
-
-
?
3-chloro-L-phenylalanine
3-chloro-trans-cinnamate + NH3
-
-
-
?
3-chloro-L-phenylalanine
3-chloro-trans-cinnamate + NH3
-
-
-
r
3-chloro-trans-cinnamate + NH3
3-chloro-L-phenylalanine
92.6% conversion
-
-
?
3-chloro-trans-cinnamate + NH3
3-chloro-L-phenylalanine
91.7% conversion
-
-
?
3-fluoro-trans-cinnamate + NH3
3-fluoro-L-phenylalanine
91.2% conversion
-
-
?
3-fluoro-trans-cinnamate + NH3
3-fluoro-L-phenylalanine
52.1% conversion
-
-
?
3-hydroxy-trans-cinnamate + NH3
3-hydroxy-L-phenylalanine
4.3.1.24 phenylalanine ammonia-lyase
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