5.1.1.1: alanine racemase
This is an abbreviated version!
For detailed information about alanine racemase, go to the full flat file.
Word Map on EC 5.1.1.1
-
5.1.1.1
-
pyridoxal
-
5'-phosphate
-
peptidoglycan
-
racemization
-
d-cycloserine
-
stearothermophilus
-
plp-dependent
-
d-amino
-
aldimine
-
d-alanyl-d-alanine
-
exosporium
-
pyridoxal-5'-phosphate-dependent
-
drug development
-
5'-phosphate-dependent
-
d-alanine:d-alanine
-
medicine
-
biotechnology
-
pharmacology
- 5.1.1.1
- pyridoxal
- 5'-phosphate
- peptidoglycan
-
racemization
- d-cycloserine
- stearothermophilus
-
plp-dependent
-
d-amino
-
aldimine
- d-alanyl-d-alanine
- exosporium
-
pyridoxal-5'-phosphate-dependent
- drug development
-
5'-phosphate-dependent
-
d-alanine:d-alanine
- medicine
- biotechnology
- pharmacology
Reaction
Synonyms
1SFT, AAR, alanine racemase, AlaR, ALR, alr-2, ALR1, ALR2, Alr2 racemase, AlrA, AlrAba, AlrBax, AlrMtb, alrTt, ARL, BA0252, BAS0238, CBL/ALR, CdAlr, cystathionine beta-lyase, D-alanine racemase, DadB, DadX, dadXOF4, dal1, EcAlr, EcCBL, EfAlaR, L-Alanine racemase, L-Alanine:D-alanine racemase, MBalr1, MBAlr2, MetC, More, MurI, OEOE_1641, PDB, Racemase, alanine, tAlaRac, TmCBL, wMelCBL
ECTree
5.1.1.1 alanine racemaseAdvanced search results
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results (Substrates Products
Substrates Products on EC 5.1.1.1 - alanine racemase
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SUBSTRATE 
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
D-lysine
L-lysine
enzyme mutant I222T/Y354W, no activity with the wild-type enzyme
-
-
?
L-2-Aminobutyrate
D-2-Aminobutyrate
0.37% of the activity with L-Ala
-
r
L-2-aminobutyric acid
D-2-aminobutyric acid
-
18% of the activity with L-Ala
-
?
L-Arg
D-Arg
-
stepwise mechanism for alanine racemase at both 25°C and at 65°C. The carbanionic intermediate is obligatory, and Arg219 may serve to destabilize it to avoid side reactions such as transamination, a detailed reaction mechanism is proposed that includes enzyme and substrate protonation states
-
r
L-arginine
D-arginine
less than 10% activity compared to L-alanine
-
-
r
L-Methionine
D-Methionine
less than 10% activity compared to L-alanine
-
-
r
L-phenylalanine
D-phenylalanine
1.1% activity compared to L-alanine
-
-
r
L-proline
D-proline
1.1% activity compared to L-alanine
-
-
r
L-valine
D-valine
less than 10% activity compared to L-alanine
-
-
r
L-Ala
?
-
enzyme provides D-Ala as an essential building block for biosynthesis of the peptidoglycan layer of the cell wall
-
-
?
L-Ala
?
-
enzyme provides D-Ala as an essential building block for biosynthesis of the peptidoglycan layer of the cell wall
-
-
?
L-Ala
?
-
enzyme provides D-Ala as an essential building block for biosynthesis of the peptidoglycan layer of the cell wall
-
-
?
L-Ala
?
-
enzyme provides D-Ala as an essential building block for biosynthesis of the peptidoglycan layer of the cell wall
-
-
?
L-Ala
D-Ala
-
the enzyme catalyzes transamination as a side function.The pyridoxal form of the enzyme is converted to the pyridoxamine form by incubation with its natural substrate, D-alanine or L-alanine, under acidic conditions: the enzyme loses its racemase activity concomitantly. The pyridoxamine form of the enzyme returns to the pyridoxal form by incubation with pyruvate at alkaline pH
-
r
L-Ala
D-Ala
-
Tyr265 and Lys39 are the catalytic bases removing alpha-hydrogen from L- and D-alanine
-
r
L-Ala
D-Ala
the enzyme catalyzes the first committed step in bacterial cell wall biosynthesis
-
?
L-Ala
D-Ala
-
the ratio of the activity for conversion of D-alanine to L-alanine to that of the reverse conversion is constantly about 0.5 in the pH range 7-9.5
-
r
L-Ala
D-Ala
-
enzyme is required for production of D-Ala, a necessary component of the bacterial cell wall
-
?
L-alanine
D-alanine
Aeromonas hydrophila subsp. hydrophila HBNUAh01 / ATCC 7966 / DSM 30187 / JCM 1027 / KCTC 2358 / NCIMB 9240
-
-
-
r
L-alanine
D-alanine
Q81VF6
-
enzyme provides D-Ala as a required compound for the synthesis of the peptidoglycan layer of the bacterial cell wall, Tolypocladium niveum requires alanine racemase for cyclosporin biosynthesis
-
r
L-alanine
D-alanine
-
alanine racemase can discriminate effectively between L-alanine and L-2-aminobutyric acid, and selectively and reversibly catalyzes L-alanine to D-alanine transformation Therefore, the enzyme shows ability of eliminating L-Ala from the reaction mixtures of L-2-aminobutyric acid biosynthesis, method optimization and evaluation in a coupled reaction with D-amino acid oxidase converting D-alanine to pyruvate stereoselectively, overview
-
-
r
L-alanine
D-alanine
-
-
responsible for the synthesis of the d-alanine moiety present in cyclosporin A and of HC-toxin
-
?
L-alanine
D-alanine
TOXG encodes an alanine racemase whose function is to synthesize D-Ala for incorporation into HC-toxin, enzyme is involved in cyclic peptide biosynthesis
-
?
L-alanine
D-alanine
catalyzes the interconversion of D-alanine and L-alanine
-
-
r
L-alanine
D-alanine
catalyzes the interconversion of D-alanine and L-alanine, highly preferred substrate
-
-
r
L-alanine
D-alanine
reversible racemization
-
-
r
L-alanine
D-alanine
first step in the biosynthesis of the peptidoglycan
-
-
?
L-alanine
D-alanine
-
The bacterium utilizes D-alanine (DAla) for synthesis of the peptidoglycan cell wall.
-
-
r
L-alanine
D-alanine
-
a major component of the alanine pathway, D-alanine is a major component in cell wall synthesis
-
-
?
L-alanine
D-alanine
catalyzes the interconversion of D-alanine and L-alanine
-
-
r
L-alanine
D-alanine
catalyzes the interconversion of D-alanine and L-alanine
-
-
r
L-alanine
D-alanine
Pseudomonas aeruginosa ATCC 15692 / DSM 22644 / CIP 104116 / JCM 14847 / LMG 12228 / 1C / PRS 101 / PAO1
-
-
-
r
L-alanine
D-alanine
-
responsible for the synthesis of the d-alanine moiety present in cyclosporin A and of HC-toxin
-
-
?
L-alanine
D-alanine
-
reversible reaction from an external aldimine in both directions via a quinonoid intermediate, overview
-
-
r
L-leucine
D-leucine
-
activity is 20% compared with L-alanine, other amino acids are not racemized
-
-
r
L-leucine
D-leucine
0.9% activity compared to L-alanine
-
-
r
L-lysine
D-lysine
less than 10% activity compared to L-alanine
-
-
r
L-lysine
D-lysine
enzyme mutant I222T/Y354W, no activity with the wild-type enzyme
-
-
?
L-serine
D-serine
less than 10% activity compared to L-alanine
-
-
r
additional information
?
-
assay method optimization and validation, overview
-
-
?
additional information
?
-
Aeromonas hydrophila subsp. hydrophila HBNUAh01 / ATCC 7966 / DSM 30187 / JCM 1027 / KCTC 2358 / NCIMB 9240
assay method optimization and validation, overview
-
-
?
additional information
?
-
-
exchange of the alpha-hydrogen of D-Ala and L-Ala with D2O
-
-
?
additional information
?
-
high specificity to L-alanine, low activity with L-arginine, L-methionine, L-lysine, L-serine, L-valine, L-proline, L-phenylalanine, L-leucine, respectively, no activity with L-histidine
-
-
?
additional information
?
-
the enzyme is absolutely specific for L-alanine compared to other L-amino acids, overview
-
-
?
additional information
?
-
the Pelagibacter ubique cystathionine beta-lyase (CBL, EC 4.4.1.13) also shows a promiscuous alanine racemase (ALR) activity. CBL catalyzes the beta-elimination of cystathionine. The ALR activity of MBP-PuCBL is 40fold lower than its CBL activity
-
-
-
additional information
?
-
-
the Pelagibacter ubique cystathionine beta-lyase (CBL, EC 4.4.1.13) also shows a promiscuous alanine racemase (ALR) activity. CBL catalyzes the beta-elimination of cystathionine. The ALR activity of MBP-PuCBL is 40fold lower than its CBL activity
-
-
-
additional information
?
-
the Pelagibacter ubique cystathionine beta-lyase (CBL, EC 4.4.1.13) also shows a promiscuous alanine racemase (ALR) activity. CBL catalyzes the beta-elimination of cystathionine. The ALR activity of MBP-PuCBL is 40fold lower than its CBL activity
-
-
-
additional information
?
-
-
purified chlamydial GlyA also exhibits racemase activity on L-Ala in vitro
-
-
?
additional information
?
-
Alr2 can interconvert L- and D-serine and Alr2 binds to L- and D-serine with 2fold weaker affinity to that of L- and D-alanine, cf. EC 5.1.1.18
-
-
?
additional information
?
-
-
Alr2 can interconvert L- and D-serine and Alr2 binds to L- and D-serine with 2fold weaker affinity to that of L- and D-alanine, cf. EC 5.1.1.18
-
-
?
additional information
?
-
Alr2 converts L-serine to an approximately equal amount of D-serine. When tested with D-serine, Alr2 does not convert as much, and nearly 75% of the D-serine remains in the D-form
-
-
?
additional information
?
-
-
Alr2 converts L-serine to an approximately equal amount of D-serine. When tested with D-serine, Alr2 does not convert as much, and nearly 75% of the D-serine remains in the D-form
-
-
?
additional information
?
-
Alr2 can interconvert L- and D-serine and Alr2 binds to L- and D-serine with 2fold weaker affinity to that of L- and D-alanine, cf. EC 5.1.1.18
-
-
?
additional information
?
-
Alr2 converts L-serine to an approximately equal amount of D-serine. When tested with D-serine, Alr2 does not convert as much, and nearly 75% of the D-serine remains in the D-form
-
-
?
additional information
?
-
the Escherichia coli cystathionine beta-lyase (CBL, EC 4.4.1.13) also shows a promiscuous alanine racemase (ALR) activity. CBL catalyzes the beta-elimination of cystathionine
-
-
-
additional information
?
-
-
the Escherichia coli cystathionine beta-lyase (CBL, EC 4.4.1.13) also shows a promiscuous alanine racemase (ALR) activity. CBL catalyzes the beta-elimination of cystathionine
-
-
-
additional information
?
-
-
the enzyme catalyzes transamination as side reaction, R-isomer preference in the hydrogen abstraction from pyridoxamine 5'-phosphate
-
?
additional information
?
-
-
the epsilon-amino group of Lys39 participates in both racemization and transamination when catalyzed by the wild-type enzyme
-
?
additional information
?
-
residues Ile222 and Tyr354 are important for the enzyme substrate specificity
-
-
?
additional information
?
-
-
residues Ile222 and Tyr354 are important for the enzyme substrate specificity
-
-
?
additional information
?
-
-
no racemization of L-Ser, L-Asp, L-Glu, L-Val and L-Arg
-
?
additional information
?
-
-
the enzyme is only specific to L-alanine and L-isoleucine, and does not catalyze isomerization the other amino acids
-
-
?
additional information
?
-
-
the enzyme is only specific to L-alanine and L-isoleucine, and does not catalyze isomerization the other amino acids
-
-
?
additional information
?
-
-
alr racemase is constitutive and serves an anabolic function, dadB encoded enzyme is inducible and required for cell growth on L-Ala
-
-
?
additional information
?
-
-
alr racemase is constitutive and serves an anabolic function, dadB encoded enzyme is inducible and required for cell growth on L-Ala
-
-
?
additional information
?
-
-
two nonhomologous alanine racemase genes, one of which is associated with the catabolic function and the other of which presumably represents the biosynthetic function
-
-
?
additional information
?
-
the enzyme is a physiologically bifunctional alanine/glutamate racemase (EC 5.1.1.1/EC 5.1.1.3), it is not highly active, but it is clearly sufficient. The metC encoded L-alanine/L-glutamate racemase is a multifunctional CBL/ALR. CBL (EC 4.4.1.13) activity is no longer required in these bacteria
-
-
-
additional information
?
-
-
the enzyme is a physiologically bifunctional alanine/glutamate racemase (EC 5.1.1.1/EC 5.1.1.3), it is not highly active, but it is clearly sufficient. The metC encoded L-alanine/L-glutamate racemase is a multifunctional CBL/ALR. CBL (EC 4.4.1.13) activity is no longer required in these bacteria
-
-
-
additional information
?
-
TmCBL is a substantially better GLR (EC 5.1.1.3) than an ALR (EC 5.1.1.1)
-
-
-
additional information
?
-
-
TmCBL is a substantially better GLR (EC 5.1.1.3) than an ALR (EC 5.1.1.1)
-
-
-
additional information
?
-
the enzyme is a physiologically bifunctional alanine/glutamate racemase (EC 5.1.1.1/EC 5.1.1.3), it is not highly active, but it is clearly sufficient. The metC encoded L-alanine/L-glutamate racemase is a multifunctional CBL/ALR. CBL (EC 4.4.1.13) activity is no longer required in these bacteria
-
-
-
additional information
?
-
TmCBL is a substantially better GLR (EC 5.1.1.3) than an ALR (EC 5.1.1.1)
-
-
-
additional information
?
-
the enzyme is a physiologically bifunctional alanine/glutamate racemase (EC 5.1.1.1/EC 5.1.1.3), it is not highly active, but it is clearly sufficient. The metC encoded L-alanine/L-glutamate racemase is a multifunctional CBL/ALR. CBL (EC 4.4.1.13) activity is no longer required in these bacteria
-
-
-
additional information
?
-
TmCBL is a substantially better GLR (EC 5.1.1.3) than an ALR (EC 5.1.1.1)
-
-
-
additional information
?
-
the enzyme is a physiologically bifunctional alanine/glutamate racemase (EC 5.1.1.1/EC 5.1.1.3), it is not highly active, but it is clearly sufficient. The metC encoded L-alanine/L-glutamate racemase is a multifunctional CBL/ALR. CBL (EC 4.4.1.13) activity is no longer required in these bacteria
-
-
-
additional information
?
-
TmCBL is a substantially better GLR (EC 5.1.1.3) than an ALR (EC 5.1.1.1)
-
-
-
additional information
?
-
-
key enzyme in cyclosporin A biosynthesis
-
-
?
additional information
?
-
-
Tolypocladium inflatum alanine racemase is able to catalyse retroaldol cleavage and transamination reactions, kinetic analysis and reaction mechanisms, overview
-
-
?
additional information
?
-
the enzyme is a physiologically bifunctional alanine/glutamate racemase (EC 5.1.1.1/EC 5.1.1.3), it is not highly active, but it is clearly sufficient. The metC encoded L-alanine/L-glutamate racemase is a multifunctional CBL/ALR. CBL (EC 4.4.1.13) activity is no longer required in these bacteria
-
-
-
additional information
?
-
the enzyme is a physiologically bifunctional alanine/glutamate racemase (EC 5.1.1.1/EC 5.1.1.3), it is not highly active, but it is clearly sufficient. The metC encoded L-alanine/L-glutamate racemase is a multifunctional CBL/ALR. CBL (EC 4.4.1.13) activity is no longer required in these bacteria
-
-
-
