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3.4.16.4: serine-type D-Ala-D-Ala carboxypeptidase

This is an abbreviated version!
For detailed information about serine-type D-Ala-D-Ala carboxypeptidase, go to the full flat file.

Word Map on EC 3.4.16.4

Reaction

Preferential cleavage: (Ac)2-L-Lys-D-Ala-/-D-Ala. Also transpeptidation of peptidyl-alanyl moieties that are N-acyl substituents of D-alanine =

Synonyms

carboxypeptidase I, CPase, D,D-carboxypeptidase, D,D-carboxypeptidase R39, D,D-dipeptidase, D-Ala-D-Ala carboxypeptidase, D-Ala-D-Ala peptidase, D-Ala-D-Ala(D,D) carboxypeptidase, D-alanine carboxypeptidase, D-alanine carboxypeptidase I, D-alanine-carboxypeptidase, D-alanyl carboxypeptidase, D-alanyl-D-alanine carboxypeptidase, D-alanyl-D-alanine carboxypeptidase/transpeptidase, D-Alanyl-D-alanine hydrolase, D-alanyl-D-alanine peptidase, D-alanyl-D-alanine transpeptidase, D-alanyl-D-alanine-carboxypeptidase, D-alanyl-D-alanine-cleaving peptidase, D-alanyl-D-alanine-cleaving-peptidase, D-alanyl-D-alanine-transpeptidase, D-amino acid amidase, DAA, Dac, dacA, DacA-1, DacB, DacC, DacD, DAP, Dbv7, DD-Carboxypeptidase, DD-CPase, DD-CPase1, DD-peptidase, DD-transpeptidase, DD-transpeptidase/penicillin-binding protein, LMM-PBP, low molecular mass penicillin binding protein, PBP, PBP 2, PBP 3, PBP 4, PBP 5, PBP 6, PBP-5*, PBP-6B, PBP1a, PBP1b, PBP2x, PBP3, PBP4, PBP4a, PBP5, PBP6, PBP6a, PBP6b, penicillin binding protein 4, penicillin binding protein 5, penicillin binding proteins, penicillin-binding protein, penicillin-binding protein 1B, penicillin-binding protein 4a, penicillin-binding protein 5, penicillin-binding protein 5a, R39 PBP, SCO4439, serine type D-alanyl-D-alanine carboxypeptidase/transpeptidase, serine-type D-Ala-D-Ala carboxypeptidase, serine-type-D-Ala-D-Ala carboxypeptidase, transpeptidase, VanX, VanXY, VanY, VanY(D) DD-carboxypeptidase, VanYD, VanYn, VC_0947, VP2468, zinc D-Ala-D-Ala carboxypeptidase

ECTree

     3 Hydrolases
         3.4 Acting on peptide bonds (peptidases)
             3.4.16 Serine-type carboxypeptidases
                3.4.16.4 serine-type D-Ala-D-Ala carboxypeptidase

Inhibitors

Inhibitors on EC 3.4.16.4 - serine-type D-Ala-D-Ala carboxypeptidase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2,3)-alpha-methylene benzylpenicillin
-
modeling of enzyme-inhibitor complex
(2-phenylethyl)boronic acid
91% residual activity at 1 mM
(2R)-2-amino-7-oxo-7-[(4,4,4-trifluoro-3-oxobutan-2-yl)amino]heptanoic acid
i.e. D-alpha-aminopimelyl-(1,1,1-trifluoro-3-amino)butan-2-one
(3-aminophenyl)boronic acid
20% residual activity at 1 mM
(3-nitrophenyl)boronic acid
82% residual activity at 1 mM
(3H)benzylpenicillin
Streptomyces pneumoniae
-
-
(3R,5R)-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3R,5R,6R)-6-methyl-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3R,5R,6S)-6-methyl-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3R,5S)-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3R,5S,6R)-3-benzyloxycarbonyl-6-methyl-4-dethia-4-oxa-penam
-
-
(3R,5S,6R)-6-methyl-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3S,5R)-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3S,5R,6S)-3-benzyloxycarbonyl-6-methyl-4-dethia-4-oxa-penam
-
-
(3S,5R,6S)-6-methyl-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3S,5S)-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(3S,5S,6R)-6-methyl-3-(furyl-2')-4-dethia-4-oxa-penam
-
-
(4-phenoxyphenyl)boronic acid
98% residual activity at 1 mM
(5-acetylthiophen-2-yl)boronic acid
88% residual activity at 1 mM
(5-chlorothiophen-2-yl)boronic acid
91% residual activity at 1 mM
(5-cyanothiophen-2-yl)boronic acid
95% residual activity at 1 mM
(5-formylthiophen-2-yl)boronic acid
99% residual activity at 1 mM
(5R,6R)-6-[[(6S)-6-carboxy-6-(glycylamino)hexanoyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
-
-
(6R,7R)-3-[(acetyloxy)methyl]-7-[(6S)-6-carboxy-6-(glycylamino)hexanoyl]amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
-
-
1,2-Ethanedithiol
-
-
1,3-propanedithiol
-
-
1-benzothiophen-2-ylboronic acid
86% residual activity at 1 mM
2,1-benzoxaborol-1(3H)-ol
45% residual activity at 1 mM
2,3-dimercapto-1-propane-sulfonic acid
-
-
2,3-dimercapto-1-propanol
-
-
2-Methylpenem
-
-
2-Phenylpenem
-
-
3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
38% residual activity at 0.5 mM
3-(acetylamino)-5-(dihydroxyboranyl)benzoic acid
50% residual activity at 1 mM
3-(benzoylamino)-5-(dihydroxyboranyl)benzoic acid
9% residual activity at 1 mM
3-(dihydroxyboranyl)-4-[(phenylacetyl)amino]benzoic acid
80% residual activity at 1 mM
3-(dihydroxyboranyl)-5-[(2,6-dimethoxybenzoyl)amino]benzoic acid
84% residual activity at 1 mM
3-(dihydroxyboranyl)-5-[(phenoxyacetyl)amino]benzoic acid
2% residual activity at 1 mM
3-(dihydroxyboranyl)-5-[(thiophen-2-ylacetyl)amino]benzoic acid
5% residual activity at 1 mM
3-(dihydroxyboranyl)-5-[(thiophen-2-ylcarbonyl)amino]benzoic acid
18% residual activity at 1 mM
3-(dihydroxyboryl)-5-(2-methoxybenzamido)benzoic acid
10% residual acvtivity at 1 mM
3-(dihydroxyboryl)-5-(2-phenylacetamido)benzoic acid
3% residual acvtivity at 1 mM
3-(dihydroxyboryl)benzoic acid
20% residual acvtivity at 1 mM
3-(N-glycyl-L-cysteinyl)-N-ethylpropionamide
-
-
3-(trifluoroacetyl)benzoic acid
60% residual activity at 1 mM
3-formylbenzoic acid
77% residual activity at 1 mM
4-(dihydroxyboranyl)benzoic acid
85% residual activity at 1 mM
4-chloromercuribenzoate
-
complete inhibition at 1 mM
4-[(phenylacetyl)amino]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid
81% residual activity at 1 mM
5-(dihydroxyboranyl)thiophene-2-carboxylic acid
57% residual activity at 1 mM
6-beta(alpha-N-acetyl-L-lysyl)-aminopenicillanic acid
-
-
6-beta(D-alpha-aminopimelyl)-aminopenicillanic acid
6-beta(D-alpha-aminosuberyl)-aminopenicillanic acid
6-beta(N-acetyl-L-alanyl-gamma-D-glutamyl-L-alanyl)-aminopenicillanic acid
-
-
7-(phenoxyacetamido)-3-desacetoxycephalosporamic acid
-
-
7-beta(alpha-N-acetyl-L-lysyl)-aminocephalosporanic acid
-
-
7-beta(D-alpha-aminopimelyl)-aminocephalosporanic acid
alpha-N-glycyl-epsilon-N-acetyl-L-lysine
-
inhibits hydrolysis of 3-(N-glycyl-L-cysteinyl)-propanoyl-D-alanyl-D-thiolactate
amoxicillin
-
-
ampicillin
arylakylidene imino-thiazolidin-4-ones 10
-
86% inhibition
arylakylidene imino-thiazolidin-4-ones 11
-
82% inhibition
arylakylidene imino-thiazolidin-4-ones 12
-
64% inhibition
arylakylidene imino-thiazolidin-4-ones 13
-
83% inhibition
arylakylidene imino-thiazolidin-4-ones 16
-
100% inhibition
arylakylidene imino-thiazolidin-4-ones 17
-
100% inhibition
arylakylidene imino-thiazolidin-4-ones 18
-
96% inhibition
arylakylidene imino-thiazolidin-4-ones 19
-
84% inhibition
arylakylidene imino-thiazolidin-4-ones 5
-
89% inhibition
arylakylidene imino-thiazolidin-4-ones 6
-
92% inhibition
arylakylidene imino-thiazolidin-4-ones 8
-
99% inhibition
arylakylidene imino-thiazolidin-4-ones 9
-
85% inhibition
arylalkylidene rhodanine derivative 1
-
88% inhibition
arylalkylidene rhodanine derivative 2
arylalkylidene rhodanine derivative 3
-
83% inhibition
arylalkylidene rhodanine derivative 4
-
95% inhibition
ayercillin
-
dipeptide-releasing activity is penicillin sensitive
benzylpenicillin
beta-lactam
beta-lactams
-
biphenyl-4,4'-diyldiboronic acid
97% residual activity at 0.1 mM
Boc-gamma-D-Glu-L-Lys-(Cbz)-D-boroAla-(-)-pinanediol
effective inhibitor of the D-alanine CPase activity of PBP5
carbenicillin
-
-
cefaclor
-
-
cefadroxil
-
-
cefalexin
-
-
cefalothin
-
-
cefmetazole
-
-
cephalexin
-
-
cephalosporidin
-
-
cephalosporin
cephalosporin C
classical non-specific beta-lactam
cephalothin
cetyltrimethylammonium bromide
-
-
Cloxacillin
-
-
D-Ala(P,O)D-Ala
-
acts as slow binding inhibitor
D-Ala(P,O)D-Phe
-
acts as slow binding inhibitor
D-alpha-phenylpropionate
-
-
D-cysteine
-
-
D-hexahydromandelate
-
-
D-mandelate
-
-
D-phenyllactate
-
-
Delta2-(and Delta3)-Deacetoxy-7-phenylacetamidocephalosporanates
-
-
-
depsipeptides
-
-
-
diacetyl-L-Lys-D-Ala
-
-
Dicloxacillin
-
-
diisopropyl fluorophosphate
-
1 mM, 28% inhibition
dithiothreitol
-
-
EDTA
4 mM, complete loss of activity. Ativity may be restored in presence of 8 mM Zn2+
epsilon-N-glycyl-alpha-N-acetyl-L-alanyl-D-isoglutaminyl-L-lysine
-
inhibits hydrolysis of 3-(N-glycyl-L-cysteinyl)-propanoyl-D-alanyl-D-thiolactate
formaldehyde
-
1 mM, 53% inhibition
glycolyl-L-Phe
-
-
iodoacetamide
-
1 mM, 20% inhibition
L-cysteine
-
-
Mercaptosuccinic acid
-
-
Methicillin
Moenomycin
N,N-diacetyl-L-Lys-D-Ala-D-Ala
Streptomyces pneumoniae
-
inhibition of PBP3 by its own substrate above a ligand concentration of 15 mM
N-(glycyl)-D,L-alpha-aminocaprylic acid
-
inhibits hydrolysis of 3-(N-glycyl-L-cysteinyl)-propanoyl-D-alanyl-D-thiolactate
N-benzoyl-beta-sultam
time-dependent, irreversible active site directed inhibitor, the rate of inactivation is first order with respect to beta-sultam concentration and second order rate constants show dependence on pH
N-Chlorosuccinimide
-
1 mM, 50% inhibition
N-p-chloro-beta-sultam
-
N-p-methoxy-beta-sultam
least effective inhibitor
N-p-nitro-beta-sultam
-
Nalpha-tert-butoxycarbonyl-Nepsilon-benzyloxycarbonyl-L-Lys-D-Ala-D-Ala
-
substrate inhibition above 30 mM
NEM
-
1 mM, complete inhibition
nocardicin A
Oxyimino-DELTA3-cephalosporins
-
p-hydroxymercuribenzoate
-
1 mM, complete inhibition
Penicillanate
-
-
penicillin
penicillin G
Penicillin V
-
-
phenoxymethylpenicillin
-
-
phenyl glycyl-L-alpha-aminopimelyl-epsilon-(D-2-aminoethyl)phosphonate
-
phenylboronic acid
piperacillin
sulfazecine
thiophen-2-ylboronic acid
88% residual activity at 1 mM
thiosalicylic acid
-
-
Vancomycin
-
vancomycin derivatives inhibit the glycosyl transferase activity
[3-([[5-(dimethylamino)naphthalen-1-yl]sulfonyl]amino)phenyl]boronic acid
60% residual activity at 0.5 mM
[3-[(2,6-dimethoxybenzoyl)amino]-5-(methoxycarbonyl)thiophen-2-yl]boronic acid
98% residual activity at 1 mM
additional information
-