Information on EC 3.1.1.43 - alpha-amino-acid esterase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
3.1.1.43
-
RECOMMENDED NAME
GeneOntology No.
alpha-amino-acid esterase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an alpha-amino acid ester + H2O = an alpha-amino acid + an alcohol
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
ester hydrolysis
-
alpha-beta hydrolase, classical catalytic triade with S205 as the nucleophile
hydrolysis of carboxylic ester
SYSTEMATIC NAME
IUBMB Comments
alpha-amino-acid-ester aminoacylhydrolase
Also catalyses alpha-aminoacyl transfer to a number of amine nucleophiles.
CAS REGISTRY NUMBER
COMMENTARY hide
74506-40-4
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
gene aehR
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Protaminobacter alboflavus
-
-
-
Manually annotated by BRENDA team
Protaminobacter alboflavus IFO 13221
-
-
-
Manually annotated by BRENDA team
Pseudomonas danceae
-
-
-
Manually annotated by BRENDA team
Pseudomonas melanogenum
Pseudomonas melanogenum ATCC 17808
-
-
-
Manually annotated by BRENDA team
Pseudomonas melanogenum IFO 12020
-
-
-
Manually annotated by BRENDA team
Pseudomonas melanogenum KY3987
-
-
-
Manually annotated by BRENDA team
Pseudomonas melanogenum KY8540
a beta-lactamase deficient mutant strain
-
-
Manually annotated by BRENDA team
pv. campestris, gene gaa
-
-
Manually annotated by BRENDA team
pv. campestris, gene gaa
-
-
Manually annotated by BRENDA team
gene aehX
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
physiological function
-
hVACVase is a prodrug-activating enzyme for amino acid prodrugs including the antiviral drugs valacyclovir and valganciclovir
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
3-amino-3-phenylpropionic acid ethyl ester + H2O
?
show the reaction diagram
-
-
-
-
?
4-carbamimidamidobenzyl L-isoleucinate + H2O
L-isoleucine + 1-[4-(hydroxymethyl)phenyl]guanidine
show the reaction diagram
-
-
-
-
?
4-carbamimidamidobenzyl L-phenylalaninate + H2O
L-phenylalanine + 1-[4-(hydroxymethyl)phenyl]guanidine
show the reaction diagram
-
-
-
-
?
4-carbamimidamidobenzyl L-valinate + H2O
L-valine + 1-[4-(hydroxymethyl)phenyl]guanidine
show the reaction diagram
-
-
-
-
?
4-hydroxy-D-phenylglycine methyl ester + H2O
4-hydroxy-D-phenylglycine + methanol
show the reaction diagram
5'-O-L-valyl-2'-deoxy-5-fluorouridine + H2O
L-valine + 2'-deoxy-5-fluorouridine
show the reaction diagram
-
-
-
-
?
acetyl-D-phenyl methyl ester + L-leucine amide
acetyl-D-phenyl-L-leucine + methanol
show the reaction diagram
-
-
-
?
acetyl-D-phenyl methyl ester + L-phenylalanine amide
acetyl-D-phenyl-L-phenylalanine + methanol
show the reaction diagram
-
-
-
?
acetyl-D-phenylalanine methyl ester + H2O
acetyl-D-phenylalanine + methanol
show the reaction diagram
-
-
-
r
acetyl-L-phenylalanine methyl ester + H2O
acetyl-L-phenylalanine + methanol
show the reaction diagram
-
-
-
r
alpha-aminoisobutyric acid methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
alpha-aminoisobutyric acid methyl ester + H2O
alpha-aminoisobutyric acid + methanol
show the reaction diagram
amoxicillin + H2O
D-4-hydroxyphenylglycine amide + 6-aminopenicillanic acid
show the reaction diagram
ampicillin + H2O
(R)-2-phenylglycine + 6-aminopenicillanic acid
show the reaction diagram
an alpha-aminoacid ester + H2O
an alpha-amino acid + an alcohol
show the reaction diagram
beta-Ala benzyl ester + H2O
beta-Ala + benzoic acid
show the reaction diagram
-
-
-
-
?
cefadroxil + H2O
?
show the reaction diagram
cefaloglycin + H2O
?
show the reaction diagram
cefatrizine + H2O
?
show the reaction diagram
-
-
-
-
?
cefradine + H2O
?
show the reaction diagram
Pseudomonas melanogenum
-
hydrolysis
-
-
?
cephalexin + H2O
7-amino-3-deacetoxycephalosporanic acid + phenylglycine
show the reaction diagram
cephalexin + H2O
D-phenylglycine + 7-aminodesacetoxycephalosporanic acid
show the reaction diagram
cephaloglycin + H2O
?
show the reaction diagram
-
-
-
-
?
D-2-nitro-5-[(phenylglycyl)amino]benzoic acid + H2O
phenylglycine + p-nitrophenol
show the reaction diagram
-
-
r
D-4-hydroxyphenylglycine methyl ester + H2O
D-4-hydroxyphenylglycine + methanol
show the reaction diagram
-
-
-
-
?
D-alanine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
D-alanine methyl ester + H2O
D-alanine + methanol
show the reaction diagram
D-alpha-phenylglycine ethyl ester + 7-amino-3-deacetoxycephalosporanic acid
ethanol + cephalexin
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine ethyl ester + H2O
D-alpha-phenylglycine + ethanol
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine isopropyl ester + 7-amino-3-deacetoxycephalosporanic acid
isopropanol + cephalexin
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine isopropyl ester + H2O
D-alpha-phenylglycine + isopropanol
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine methyl ester + 6-aminopenicillanic acid
methanol + ?
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + cephalexin
show the reaction diagram
D-alpha-phenylglycine methyl ester + 7-aminocephalosporanic acid
methanol + ?
show the reaction diagram
D-alpha-phenylglycine methyl ester + H2O
D-alpha-phenylglycine + methanol
show the reaction diagram
D-alpha-phenylglycine n-butyl ester + 7-amino-3-deacetoxycephalosporanic acid
butanol + cephalexin
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine n-butyl ester + H2O
D-alpha-phenylglycine + n-butanol
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine n-propyl ester + 7-amino-3-deacetoxycephalosporanic acid
n-propanol + cephalexin
show the reaction diagram
-
-
-
?
D-alpha-phenylglycine n-propyl ester + H2O
D-alpha-phenylglycine + n-propanol
show the reaction diagram
-
-
-
?
D-aspartate dimethyl ester + H2O
D-aspartate + methanol
show the reaction diagram
-
-
-
r
D-leucine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
D-leucine methyl ester + H2O
D-leucine + methanol
show the reaction diagram
-
-
-
?
D-methionine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
D-methionine methyl ester + H2O
D-methionine + methanol
show the reaction diagram
D-phenylalanine amide + H2O
D-phenylalanine + NH3
show the reaction diagram
-
-
-
?
D-phenylalanine methyl ester + H2O
D-phenylalanine + methanol
show the reaction diagram
-
-
-
r
D-phenylglycine amide + H2O
D-phenylglycine + NH3
show the reaction diagram
D-phenylglycine methyl ester + 6-amino penicillanic acid
ampicillin
show the reaction diagram
-
specific for D-isomer
-
?
D-phenylglycine methyl ester + 7-amino-desacetoxycephalosporanic acid
cephalexin + H2O
show the reaction diagram
-
-
-
r
D-phenylglycine methyl ester + H2O
D-phenylglycine + methanol
show the reaction diagram
D-serine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
D-serine methyl ester + H2O
D-serine + methanol
show the reaction diagram
-
-
-
?
D-tryptophan methyl ester + H2O
D-tryptophan + methanol
show the reaction diagram
-
-
-
r
D-tyrosine methyl ester + H2O
D-tyrosine + methanol
show the reaction diagram
-
-
-
r
DL-alpha-aminobutyric acid methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
DL-alpha-aminobutyric acid methyl ester + H2O
DL-alpha-aminobutyric acid + methanol
show the reaction diagram
-
-
-
?
DL-phenylglycine methyl ester + 6-amino penicillanic acid
ampicillin
show the reaction diagram
-
more than 85% of D-phenylglycine methyl ester is transformed into ampicillin
-
?
DL-threonine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
DL-threonine methyl ester + H2O
DL-threonine + methanol
show the reaction diagram
-
-
-
?
floxuridine + H2O
?
show the reaction diagram
-
-
-
-
?
gemcitabine + H2O
?
show the reaction diagram
-
-
-
-
?
Gly benzyl ester + H2O
Gly + benzoic acid
show the reaction diagram
-
-
-
-
?
glycine ethyl ester + 7-aminocephalosporanic acid
ethanol + ?
show the reaction diagram
-
-
-
?
glycine ethyl ester + H2O
glycine + ethanol
show the reaction diagram
-
-
-
?
glycine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
glycine methyl ester + H2O
glycine + methanol
show the reaction diagram
-
-
-
?
L-Ala benzyl ester + H2O
L-Ala + benzoic acid
show the reaction diagram
-
-
-
-
?
L-alpha-phenylglycine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + cephalexin
show the reaction diagram
-
-
-
?
L-arginine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
L-arginine methyl ester + H2O
L-arginine + methanol
show the reaction diagram
-
-
-
?
L-aspartate dimethyl ester + H2O
L-aspartate + methanol
show the reaction diagram
-
-
-
?
L-cysteine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
L-cysteine methyl ester + H2O
L-cysteine + methanol
show the reaction diagram
L-glutamic acid methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
L-glutamic acid methyl ester + H2O
L-glutamic acid + methanol
show the reaction diagram
-
-
-
?
L-Leu benzyl ester + H2O
L-leu + benzoic acid
show the reaction diagram
-
-
-
-
?
L-leucine ethyl ester + H2O
L-leucine + ethanol
show the reaction diagram
-
-
-
?
L-lysine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
L-lysine methyl ester + H2O
L-lysine + methanol
show the reaction diagram
-
-
-
?
L-Met methyl ester + H2O
?
show the reaction diagram
-
-
-
-
?
L-methionine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
L-methionine methyl ester + H2O
L-methionine + methanol
show the reaction diagram
L-Phe benzyl ester + H2O
L-Phe + benzoic acid
show the reaction diagram
-
-
-
-
?
L-Phe ethyl ester + H2O
?
show the reaction diagram
-
-
-
-
?
L-phenylalanine ethyl ester + H2O
L-phenylalanine + ethanol
show the reaction diagram
-
-
-
?
L-phenylalanine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
-
-
-
?
L-phenylalanine methyl ester + H2O
L-phenylalanine + methanol
show the reaction diagram
L-Pro benzyl ester + H2O
L-Pro + benzoic acid
show the reaction diagram
-
-
-
-
?
L-Ser benzyl ester + H2O
L-Ser + benzoic acid
show the reaction diagram
-
-
-
-
?
L-serine methyl ester + 7-amino-3-deacetoxycephalosporanic acid
methanol + ?
show the reaction diagram
L-serine methyl ester + H2O
L-serine + methanol
show the reaction diagram
L-Trp benzyl ester + H2O
L-Trp + benzoic acid
show the reaction diagram
-
-
-
-
?
L-tryptophan methyl ester + H2O
L-tryptophan + methanol
show the reaction diagram
-
-
-
r
L-Tyr benzyl ester + H2O
L-Tyr + benzoic acid
show the reaction diagram
-
-
-
-
?
L-tyrosine ethyl ester + H2O
L-tyrosine + ethanol
show the reaction diagram
-
-
-
?
L-tyrosine methyl ester + H2O
L-tyrosine + methanol
show the reaction diagram
-
-
-
r
L-tyrosine propyl ester + H2O
L-tyrosine + propanol
show the reaction diagram
-
-
-
?
L-Val benzyl ester + H2O
L-Val + benzoic acid
show the reaction diagram
-
-
-
-
?
methyl acetate
acetate + methanol
show the reaction diagram
-
1.1% of activity with D-phenylalanine methylester
-
?
methyl butyrate
butyrate + methanol
show the reaction diagram
-
3.6% of activity with D-phenylalanine methylester
-
?
methyl caproate
caproate + methanol
show the reaction diagram
-
2% of activity with D-phenylalanine methylester
-
?
methyl caprylate
caprylate + methanol
show the reaction diagram
-
1.1% of activity with D-phenylalanine methylester
-
?
methyl propionate
propionate + methanol
show the reaction diagram
-
2.7% of activity with D-phenylalanine methylester
-
?
p-hydroxyphenylpropionic acid ethyl ester + H2O
p-hydroxyphenylpropionic acid + ethanol
show the reaction diagram
-
-
-
?
p-nitrophenyl-p'-guanidino benzoate + H2O
p-guanidino benzoate + p-nitrophenol
show the reaction diagram
-
-
-
?
phenylalanine benzyl ester + H2O
L-phenylalanine + benzyl alcohol
show the reaction diagram
-
-
-
-
?
phenylalanine ethyl ester + H2O
L-phenylalanine + ethanol
show the reaction diagram
-
-
-
-
?
phenylalanine methyl ester + H2O
L-phenylalanine + methanol
show the reaction diagram
-
-
-
-
?
phenylalanine [3-(hydroxymethyl)phenyl]guanidine + H2O
L-phenylalanine + [3-(hydroxymethyl)phenyl]guanidine
show the reaction diagram
-
-
-
-
?
valacyclovir + H2O
?
show the reaction diagram
valacyclovir + H2O
L-valine + 2-amino-9-[(2-hydroxyethyloxy)methyl]-1,9-dihydro-6H-purin-6-one
show the reaction diagram
-
-
-
-
?
valacyclovir + H2O
L-valine + acyclovir
show the reaction diagram
-
-
-
-
?
valganciclovir + H2O
?
show the reaction diagram
-
-
-
-
?
valganciclovir + H2O
L-valine + 2-amino-9-[[(1,3-dihydroxpropan-2-yl)oxy]methyl]-1,9-dihydro-6H-purin-6-one
show the reaction diagram
-
-
-
-
?
valganciclovir + H2O
L-valine + ganciclovir
show the reaction diagram
-
-
-
-
?
valine 4-nitrobenzyl ester + H2O
L-valine + 4-nitrobenzyl alcohol
show the reaction diagram
-
-
-
-
?
valine benzyl ester + H2O
L-valine + benzyl alcohol
show the reaction diagram
-
-
-
-
?
valine [3-(aminomethyl)phenyl]guanidine + H2O
L-valine + [3-(aminomethyl)phenyl]guanidine
show the reaction diagram
-
-
-
-
?
valine [3-(hydroxymethyl)phenyl]guanidine + H2O
L-valine + [3-(hydroxymethyl)phenyl]guanidine
show the reaction diagram
-
-
-
-
?
zidovudine + H2O
?
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
an alpha-aminoacid ester + H2O
an alpha-amino acid + an alcohol
show the reaction diagram
valacyclovir + H2O
?
show the reaction diagram
-
stereospecific reaction
-
-
?
valacyclovir + H2O
L-valine + acyclovir
show the reaction diagram
-
-
-
-
?
valganciclovir + H2O
L-valine + ganciclovir
show the reaction diagram
-
-
-
-
?
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
HgCl2
-
activates
Mg2+
-
-
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
7-amino-3-deacetoxycephalosporanic acid
-
hydrolysis of D-alpha-phenylglycine methyl ester
ampicillin
-
hydrolysis, substrate inhibition
ethyl D-alpha-aminophenylacetate
-
hydrolysis, substrate inhibition
methyl D-alpha-aminophenylacetate
-
hydrolysis, substrate inhibition
p-nitrophenyl-p'-guanidino benzoate
-
reversible inactivation
phenylmethanesulfonyl fluoride
-
1 mM, 99% inhibition
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ethylene glycol
-
addition of ethylene glycol at 33 vol% to the reaction medium for cephalexin synthesis improves the yield from 70% to 95%
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.009
4-carbamimidamidobenzyl L-isoleucinate
-
pH 7.4, 37°C
0.207
4-carbamimidamidobenzyl L-phenylalaninate
-
pH 7.4, 37°C
0.046
4-carbamimidamidobenzyl L-valinate
-
pH 7.4, 37°C
0.011
4-hydroxy-D-phenylglycine methyl ester
-
pH 6.0, 30°C, recombinant enzyme
5.08
7-amino-3-deacetoxycephalosporanic acid
-
-
0.0026 - 2.6
amoxicillin
0.0006 - 1
ampicillin
0.00034 - 1.7
cefadroxil
0.0017 - 0.00196
cefaloglycin
0.001
cefatrizine
-
below, hydrolysis, pH 6.4, 25°C, recombinant enzyme
0.00179
cefradine
Pseudomonas melanogenum
-
pH 6.0, 37°C
0.00035 - 2.99
cephalexin
1.1
D-2-nitro-5-[(phenylglycyl)amino]benzoic acid
30°C, pH 6.2
63 - 292
D-4-hydroxyphenylglycine methyl ester
40.9
D-alanine methyl ester
-
-
8.26
D-alpha-phenylglycine methyl ester
-
-
0.013 - 13
D-phenylglycine amide
0.0026 - 7
D-phenylglycine methyl ester
2.6
ethyl DL-alpha-amino-n-butyrate
-
-
5
glycine ethyl ester
-
-
0.5
L-S-benzylcysteine ethyl ester
-
-
0.8
L-valine methyl ester
-
-
4.3
methyl D-alpha-aminophenylacetate
-
-
32.2
methyl DL-alpha-aminoisobutyrate
-
-
24
methyl L-alpha-aminophenylacetate
-
-
0.099
phenylalanine benzyl ester
-
pH 7.4, 37°C, recombinant enzyme
6.7
phenylalanine ethyl ester
-
pH 7.4, 37°C, recombinant enzyme
5.14
phenylalanine methyl ester
-
pH 7.4, 37°C, recombinant enzyme
0.207
phenylalanine [3-(hydroxymethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
0.00006 - 0.068
valacyclovir
0.0019
valganciclovir
-
pH 7.4, 37°C, recombinant enzyme
0.014
valine 4-nitrobenzyl ester
-
pH 7.4, 37°C, recombinant enzyme
0.06
valine benzyl ester
-
pH 7.4, 37°C, recombinant enzyme
1.81
valine [3-(aminomethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
0.046
valine [3-(hydroxymethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
14
4-carbamimidamidobenzyl L-isoleucinate
-
pH 7.4, 37°C
345
4-carbamimidamidobenzyl L-phenylalaninate
-
pH 7.4, 37°C
154
4-carbamimidamidobenzyl L-valinate
-
pH 7.4, 37°C
263
4-hydroxy-D-phenylglycine methyl ester
-
pH 6.0, 30°C, recombinant enzyme
10
amoxicillin
17.5 - 162
ampicillin
9.6 - 347
cefadroxil
9.6
cefaloglycin
-
pH 6.0, 30°C, recombinant enzyme
2.3
cefatrizine
-
hydrolysis, pH 6.4, 25°C, recombinant enzyme
71 - 3200
cephalexin
0.4
D-2-nitro-5-[(phenylglycyl)amino]benzoic acid
30°C, pH 6.2
147 - 613
D-4-hydroxyphenylglycine methyl ester
6600 - 11100
D-alpha-phenylglycine methyl ester
1.6 - 43
D-phenylglycine amide
982 - 1860
D-phenylglycine methyl ester
395
phenylalanine benzyl ester
-
pH 7.4, 37°C, recombinant enzyme
93
phenylalanine ethyl ester
-
pH 7.4, 37°C, recombinant enzyme
228
phenylalanine methyl ester
-
pH 7.4, 37°C, recombinant enzyme
6160
phenylalanine methylester
-
25°C, pH 7.0
345
phenylalanine [3-(hydroxymethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
58 - 126
valacyclovir
101
valganciclovir
-
pH 7.4, 37°C, recombinant enzyme
130
valine 4-nitrobenzyl ester
-
pH 7.4, 37°C, recombinant enzyme
60
valine benzyl ester
-
pH 7.4, 37°C, recombinant enzyme
0.0023
valine [3-(aminomethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
154
valine [3-(hydroxymethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1580
4-carbamimidamidobenzyl L-isoleucinate
-
pH 7.4, 37°C
1660
4-carbamimidamidobenzyl L-phenylalaninate
-
pH 7.4, 37°C
3370
4-carbamimidamidobenzyl L-valinate
-
pH 7.4, 37°C
24
4-hydroxy-D-phenylglycine methyl ester
-
pH 6.0, 30°C, recombinant enzyme
3.9
amoxicillin
-
pH 6.0, 30°C, recombinant enzyme
30 - 162
ampicillin
1021
cefadroxil
-
pH 6.0, 30°C, recombinant enzyme
6
cefaloglycin
-
pH 6.0, 30°C, recombinant enzyme
95 - 1100
cephalexin
0.0018 - 0.0096
D-4-hydroxyphenylglycine methyl ester
3.3
D-phenylglycine amide
-
above, pH 6.2, 27-30°C
148 - 1300
D-phenylglycine methyl ester
3980
phenylalanine benzyl ester
-
pH 7.4, 37°C, recombinant enzyme
14
phenylalanine ethyl ester
-
pH 7.4, 37°C, recombinant enzyme
44
phenylalanine methyl ester
-
pH 7.4, 37°C, recombinant enzyme
1660
phenylalanine [3-(hydroxymethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
213 - 850
valacyclovir
53
valganciclovir
-
pH 7.4, 37°C, recombinant enzyme
9490
valine 4-nitrobenzyl ester
-
pH 7.4, 37°C, recombinant enzyme
992
valine benzyl ester
-
pH 7.4, 37°C, recombinant enzyme
0.0013
valine [3-(aminomethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
3370
valine [3-(hydroxymethyl)phenyl]guanidine
-
pH 7.4, 37°C, recombinant enzyme
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.6
-
3-amino-3-phenylpropionic acid ethyl ester
1.8
-
beta-Ala benzyl ester
35.3
-
L-Trp benzyl ester
41.4
-
L-Tyr benzyl ester
75.3
-
L-Phe ethyl ester
103.7
-
valacyclovir
156.2
-
L-Met methyl ester
156.3
-
L-Val benzyl ester
358.3
-
L-Phe benzyl ester
484.3
-
L-Ser benzyl ester
635
-
L-Leu benzyl ester
667
Cephalexin synthesis
849.4
-
L-Gly benzyl ester
1368
-
L-Ala benzyl ester
5148
-
L-Pro benzyl ester
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 6
Pseudomonas melanogenum
-
strain KY3987, ampicillin synthesis
6 - 6.25
-
assay at
6 - 6.5
6
Pseudomonas melanogenum
-
ampicillin synthesis and hydrolysis
6 - 6.4
-
synthesis and hydrolysis of cephalexin and D-phenylglycine methyl ester
6.1 - 6.2
-
synthesis and hydrolysis of cephalexin and D-phenylglycine methyl ester
6.4
-
hydrolysis and acyl group transfer
6.8
-
ampicillin hydrolysis
7.4 - 8
-
valacyclovir hydrolysis in vitro
7.6
-
hydrolysis of phenylalanine methylester
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 11
-
approx. 10% of maximal activity at pH 4.0 and pH 10.0, respectively
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 37
35
-
hydrolysis and acyl group transfer
35 - 45
40
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10 - 65
-
40% of maximal activity at 10°C, approx. 5% of maximal activity at 65°C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7
-
isoelectric focusing
7.2
Pseudomonas melanogenum
-
-
8
-
above
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
27000
-
2 * 27000; 2 * 27000, in crystals and solution
29000
-
x * 29000
39000
-
4 * 39000, SDS-PAGE
68000
-
4 * 68000
70915
-
4 * 70915, deduced from nucleotide sequence
76000
-
4 * 76000, SDS-PAGE
146000
Pseudomonas melanogenum
-
-
150000
dynamic light scattering
160000
-
gel filtration
270000 - 280000
-
ultracentrifugation, gel filtration
280000 - 290000
-
-
300000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
homodimer
homotetramer
monomer or dimer
-
x * 29000
tetramer
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
no modification
-
no glycoprotein
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
5 mg/ml AEH in 50 mM sodium phosphate, pH 6.2 is mixed with 0.003 ml 15-17% polyethylene glycol 4000, 200 mM ammonium acetate, 100 mM sodium acetate, ph 4.5, followed by equilibration agains this polyethylene glycol solution, crystals diffract to 2.0 A
-
the crystal structures of the native protein, the S122A and D123N mutants, and the native enzyme in complex with L-tyrosine amide are solved at resolutions of 1.75 A, 1.90 A, 1.85 A and 1.90 A, respectively
-
0.0015 ml of concentrated AEH is mixed with an equal volume of 12-15% polyethylene glycol 8000 in 100 mM cacodylate, pH 6.5, and equilibrated against 0.5 ml of this precipitant solution, crystals diffract to 1.9A
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 9
-
stable, 16 h, 0°C
80934
5.5 - 7.5
-
stable, 1 h, 30°C
80934
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
-
no loss of activity after 15 min, pH 6
50
-
completely inactivated within 15 min, pH 6
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
soluble enzyme is very rapidly inactivated
-
ORGANIC SOLVENT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
1,1,2-trichloroethane
-
50% v/v solution: 80% of maximal activity in hydrolysis of cephalexin
2,3-butanediol
-
50% v/v solution: 31% of maximal activity in hydrolysis of cephalexin, 44% of maximal activity in synthesis of cephalexin
2-heptanone
-
50% v/v solution: 105% of maximal activity in hydrolysis of cephalexin, 37% of maximal activity in synthesis of cephalexin
2-octanone
-
50% v/v solution: 101% of maximal activity in hydrolysis of cephalexin, 101% of maximal activity in synthesis of cephalexin
acetophenone
-
50% v/v solution: 57% of maximal activity in hydrolysis of cephalexin
butyl acetate
-
50% v/v solution: 106% of maximal activity in hydrolysis of cephalexin
chlorobenzene
-
50% v/v solution: 71% of maximal activity in hydrolysis of cephalexin
chloroform
-
50% v/v solution: 86% of maximal activity in hydrolysis of cephalexin
dibutyl ether
-
50% v/v solution: 113% of maximal activity in hydrolysis of cephalexin, 111% of maximal activity in synthesis of cephalexin
Ethyl acetate
-
50% v/v solution: 101% of maximal activity in hydrolysis of cephalexin, 82% of maximal activity in synthesis of cephalexin
heptane
-
50% v/v solution: 102% of maximal activity in hydrolysis of cephalexin, 117% of maximal activity in synthesis of cephalexin
hexadecane
-
50% v/v solution: 126% of maximal activity in hydrolysis of cephalexin
isopropanol
-
50% v/v solution: 18% of maximal activity in hydrolysis of cephalexin, 28% of maximal activity in synthesis of cephalexin
isopropyl acetate
-
50% v/v solution: 91% of maximal activity in hydrolysis of cephalexin, 100% of maximal activity in synthesis of cephalexin
Methanol
-
50% v/v solution: 13% of maximal activity in hydrolysis of cephalexin, 29% of maximal activity in synthesis of cephalexin
n-Butanol
-
50% v/v solution: 65% of maximal activity in hydrolysis of cephalexin, 47% of maximal activity in synthesis of cephalexin
n-decanol
-
50% v/v solution: 99% of maximal activity in hydrolysis of cephalexin
n-heptanol
-
50% v/v solution: 111% of maximal activity in hydrolysis of cephalexin, 115% of maximal activity in synthesis of cephalexin
n-nonanol
-
50% v/v solution: 102% of maximal activity in hydrolysis of cephalexin, 102% of maximal activity in synthesis of cephalexin
n-octanol
-
50% v/v solution: 110% of maximal activity in hydrolysis of cephalexin, 119% of maximal activity in synthesis of cephalexin
n-pentanol
-
50% v/v solution: 84% of maximal activity in hydrolysis of cephalexin, 73% of maximal activity in synthesis of cephalexin
phenoxy ethanol
-
50% v/v solution: 62% of maximal activity in hydrolysis of cephalexin
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ammonium sulfate, DEAE-Toyopearl, electrofocusing, Disc electrophoresis
-
CM-Sepharose, hydrophobic interaction, gel filtration
from liver
-
metal ion affinity chromatography using nickel-nitrilotriacetic acid-Agarose
recombinant AEH
recombinant AEH, Ni2+-agarose, gel filtration
-
recombinant His6-tagged hVACVase construct from Escherichia coli by affinity chromatography
-
using a S strong cation exchange and a phenyl-Sepharose hydrophobic interaction column
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
expression of His-tagged AEH in Escherichia coli
-
gene aehA, expression in Escherichia coli
-
gene aehR, expression in Escherichia coli
-
gene aehX, expression in Escherichia coli
-
gene gaa, expression in Escherichia coli
-
into the vector pET17b for expression in Escherichia coli BL21DE3 and B834DE3 cells
-
overexpression of wild-type and mutant enzymes in Escherichia coli
-
recombinant expression in Escherichia coli strain VKPM B-11246
-
recombinant expression of the His6-tagged hVACVase construct, M-S tag-PDLGTLVPRGSMGM-hVACVase-AAALE-His tag, in Escherichia coli
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D338A
-
0.07% of wild-type kcat
H370A
-
0.07% of wild-type kcat
H610A
-
more than 69% of wild-type kcat, partially purified
R85A
-
67% of wild-type kcat
S156A
-
48% of wild-type kcat
R87I
-
site-directed saturation mutagenesis
V131S
-
site-directed saturation mutagenesis; site-directed saturation mutagenesis, the mutant shows the highest initial rates of synthesis toward three p-hydroxyl cephalosporins with 23%, 17% and 64% increases in maximum product accumulation of cefadroxil, cefprozil and cefatrizine, respectively
Y175A
-
site-directed saturation mutagenesis
D123N
-
point mutant
S122A
-
point mutant
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
synthesis