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Literature summary extracted from

  • Inglis, S.R.; Zervosen, A.; Woon, E.C.; Gerards, T.; Teller, N.; Fischer, D.S.; Luxen, A.; Schofield, C.J.
    Synthesis and evaluation of 3-(dihydroxyboryl)benzoic acids as D,D-carboxypeptidase R39 inhibitors (2009), J. Med. Chem., 52, 6097-6106.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.4.16.4 (2-phenylethyl)boronic acid 91% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 (3-aminophenyl)boronic acid 20% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 (3-nitrophenyl)boronic acid 82% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 (4-phenoxyphenyl)boronic acid 98% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 (5-acetylthiophen-2-yl)boronic acid 88% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 (5-chlorothiophen-2-yl)boronic acid 91% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 (5-cyanothiophen-2-yl)boronic acid 95% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 (5-formylthiophen-2-yl)boronic acid 99% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 1-benzothiophen-2-ylboronic acid 86% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 2,1-benzoxaborol-1(3H)-ol 45% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid 38% residual activity at 0.5 mM Actinomadura sp. R39
3.4.16.4 3-(acetylamino)-5-(dihydroxyboranyl)benzoic acid 50% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(benzoylamino)-5-(dihydroxyboranyl)benzoic acid 9% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboranyl)-4-[(phenylacetyl)amino]benzoic acid 80% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboranyl)-5-[(2,6-dimethoxybenzoyl)amino]benzoic acid 84% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboranyl)-5-[(phenoxyacetyl)amino]benzoic acid 2% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboranyl)-5-[(thiophen-2-ylacetyl)amino]benzoic acid 5% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboranyl)-5-[(thiophen-2-ylcarbonyl)amino]benzoic acid 18% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboryl)-5-(2-methoxybenzamido)benzoic acid 10% residual acvtivity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboryl)-5-(2-phenylacetamido)benzoic acid 3% residual acvtivity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(dihydroxyboryl)benzoic acid 20% residual acvtivity at 1 mM Actinomadura sp. R39
3.4.16.4 3-(trifluoroacetyl)benzoic acid 60% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 3-formylbenzoic acid 77% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 4-(dihydroxyboranyl)benzoic acid 85% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 4-[(phenylacetyl)amino]-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid 81% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 5-(dihydroxyboranyl)thiophene-2-carboxylic acid 57% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 biphenyl-4,4'-diyldiboronic acid 97% residual activity at 0.1 mM Actinomadura sp. R39
3.4.16.4 additional information not inhibited by methyl 3-(dihydroxyboryl)-5-(2-phenylacetamido)benzoate Actinomadura sp. R39
3.4.16.4 phenylboronic acid 50% residual activity at 0.5 mM Actinomadura sp. R39
3.4.16.4 thiophen-2-ylboronic acid 88% residual activity at 1 mM Actinomadura sp. R39
3.4.16.4 [3-([[5-(dimethylamino)naphthalen-1-yl]sulfonyl]amino)phenyl]boronic acid 60% residual activity at 0.5 mM Actinomadura sp. R39
3.4.16.4 [3-[(2,6-dimethoxybenzoyl)amino]-5-(methoxycarbonyl)thiophen-2-yl]boronic acid 98% residual activity at 1 mM Actinomadura sp. R39

Organism

EC Number Organism UniProt Comment Textmining
3.4.16.4 Actinomadura sp. R39 P39045
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
3.4.16.4
-
 Actinomadura sp. R39

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.4.16.4 (R)-[2-(benzoylamino)propionylsulfanyl]acetic acid + H2O
-
 Actinomadura sp. R39 ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.4.16.4 D,D-carboxypeptidase R39
-
 Actinomadura sp. R39
3.4.16.4 PBP
-
 Actinomadura sp. R39
3.4.16.4 penicillin binding proteins
-
 Actinomadura sp. R39
3.4.16.4 R39 PBP
-
 Actinomadura sp. R39

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
3.4.16.4 0.023
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(dihydroxyboryl)-5-(2-methoxybenzamido)benzoic acid
3.4.16.4 0.028
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(dihydroxyboranyl)-5-[(phenoxyacetyl)amino]benzoic acid
3.4.16.4 0.032
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(dihydroxyboranyl)-5-[(thiophen-2-ylcarbonyl)amino]benzoic acid
3.4.16.4 0.034
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(benzoylamino)-5-(dihydroxyboranyl)benzoic acid
3.4.16.4 0.078
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(dihydroxyboranyl)-5-[(thiophen-2-ylacetyl)amino]benzoic acid
3.4.16.4 0.088
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(dihydroxyboryl)-5-(2-phenylacetamido)benzoic acid
3.4.16.4 0.4
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(dihydroxyboryl)benzoic acid
3.4.16.4 0.5
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 phenylboronic acid
3.4.16.4 1
-
 in 10 mM sodium phosphate buffer (pH 7.2) with 100 mM NaCl, 100 mM D-alanine, and 0.01 mg/ml bovine serum albumin for 60 min at 25°C Actinomadura sp. R39 3-(acetylamino)-5-(dihydroxyboranyl)benzoic acid