5.4.3.6: tyrosine 2,3-aminomutase
This is an abbreviated version!
For detailed information about tyrosine 2,3-aminomutase, go to the full flat file.
Word Map on EC 5.4.3.6
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5.4.3.6
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enediyne
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ammonia
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chromophore
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crocatus
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sativa
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lyases
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chondromyces
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stereochemistry
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myxobacterium
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enantioselectivity
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isomerizes
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globisporus
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peptidyl
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prosthetic
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chromoprotein
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taxus
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enantiomeric
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fluorinated
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protein-tethered
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fad-dependent
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depsipeptides
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acrylate
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pathway-specific
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toney
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lyase-like
- 5.4.3.6
-
enediyne
- ammonia
- chromophore
- crocatus
- sativa
- lyases
-
chondromyces
-
stereochemistry
-
myxobacterium
-
enantioselectivity
-
isomerizes
- globisporus
-
peptidyl
-
prosthetic
-
chromoprotein
- taxus
-
enantiomeric
-
fluorinated
-
protein-tethered
-
fad-dependent
- depsipeptides
- acrylate
-
pathway-specific
-
toney
-
lyase-like
Reaction
Synonyms
3,5-dihydro-5-methylidene-4H-imidazol-4-one-dependent aminomutase, 3,5-dihydro-5-methylidine-4H-imidazol-4-one-dependent tyrosine aminomutase, Aminomutase, tyrosine 2,3-, CmdF, MfTAM, MIO-dependent aminomutase, MIO-dependent tyrosine aminomutase, More, MxTAM, OsTAM, SgcC4, TAM, Tam1, Tyrosine alpha,beta-amino mutase, Tyrosine alpha,beta-mutase, tyrosine aminomutase
ECTree
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Substrates Products
Substrates Products on EC 5.4.3.6 - tyrosine 2,3-aminomutase
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REACTION DIAGRAM
(3S)-amino-3-(4-hydroxyphenyl)propanoate
(3R)-amino-3-(4-hydroxyphenyl)propanoate
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beta-tyrosine racemase activity
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r
L-3,4-dihydroxyphenylalanine
3-amino-3-(3,4-dihydroxyphenyl)propanoate
-
-
-
?
L-3-chlorotyrosine
3-amino-3-(3-chloro-4-hydroxyphenyl)propanoate
-
-
-
?
L-phenylalanine
L-beta-phenylalanine
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3% relative to the activity with L-tyrosine of wild-type enzyme
-
-
?
L-Tyr
?
-
formation of beta-Tyr which is the N-terminal amino acid of the antibiotic edeine
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-
?
L-tyrosine
(4-hydroxyphenyl)prop-2-enoate + NH3
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ammonia lyase activity of tyrosine aminomutase
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?
[3-deutero]-(2S,3R)-alpha-tyrosine
[3-deutero]-(2S,3S)-4'-O,2-N-di((S)-2-methylbutanoic acid)-alpha-tyrosine methyl ester + [3-deutero]-(2S,3R)-4'-O,2-N-di((S)-2-methylbutanoic acid)-alpha-tyrosine methyl ester
-
-
-
-
?
[3-deutero]-(2S,3S)-alpha-tyrosine
[3-deutero]-(2S,3S)-4'-O,2-N-di((S)-2-methylbutanoic acid)-alpha-tyrosine methyl ester + ([3-deutero]-(2S,3R)-4'-O,2-N-di((S)-2-methylbutanoic acid)-alpha-tyrosine methyl ester
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-
-
-
?
3-amino-3-(4-hydroxyphenyl)propanoate
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the enzyme isomerizes (S)-alpha-tyrosine to (R)-beta-tyrosine and is stereoselective for (R)-beta-tyrosine (85%), but also forms the (S)-beta-tyrosine enantiomer (15%) through inversion of configuration at both migration termini
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-
r
L-tyrosine
3-amino-3-(4-hydroxyphenyl)propanoate
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Oryza sativa enzyme OsTAM makes 75% beta-tyrosine and 25% 4-coumarate from alpha-tyrosine
-
-
?
L-tyrosine
3-amino-3-(4-hydroxyphenyl)propanoate
-
wild-type OsTAM from Oryza sativa preferentially isomerizes (2S)-alpha-tyrosine to (3R)-beta-tyrosine with an enantioselectivity (94% ee)
-
-
?
L-tyrosine
3-amino-3-(4-hydroxyphenyl)propanoate
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involved in the biosynthesis of the enediyne antitumor antibiotic C-1027
-
?
additional information
?
-
-
substrate specificity of recombinant wild-type and mutant enzymes, overview
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-
?
additional information
?
-
-
the 3,5-dihydro-5-methylidene-4H-imidazol-4-one (MIO) group in the enzyme's active site N-alkylates the NH2 of the alpha-amino acid substrates and promotes the removal of an intermediary NH2-MIO adduct. Concomitant removal of a beta-proton from the substrate (NH2-MIO adduct) by a catalytic tyrosine yields an acrylate intermediate. The aminomutase reaction continues by vicinal reprotonation and reamination at the alpha- and beta-carbons, respectively, of the acrylate to produce the beta-amino acid. Autocatalysis of the 3,5-dihydro-5-methylidene-4H-imidazol-4-one (MIO) cofactor through cyclization of (A/T/S)-Ser-Gly residues within the active site
-
-
?