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Literature summary extracted from

  • Sanchez-Sixto, C.; Prazeres, V.F.; Castedo, L.; Suh, S.W.; Lamb, H.; Hawkins, A.R.; Canada, F.J.; Jimenez-Barbero, J.; Gonzalez-Bello, C.
    Competitive inhibitors of Helicobacter pylori type II dehydroquinase: synthesis, biological evaluation, and NMR studies (2008), ChemMedChem, 3, 756-770.
    View publication on PubMed

Application

EC Number Application Comment Organism
4.2.1.10 medicine dehydroquinase is a target for the development of new antibiotics Helicobacter pylori

Cloned(Commentary)

EC Number Cloned (Comment) Organism
4.2.1.10 into the vector pET21a for expression in Escherichia coli BL21DE3 cells Helicobacter pylori

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(1H-1,2,3-triazol-4-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrothien-3-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-bromothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-hydroxyphenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(4-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-(thien-2-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-naphthalen-2-ylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-phenylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-pyridin-3-ylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-thiophen-3-ylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[3-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-1,4,5-trihydroxy-3-[4-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(1-benzofuran-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(1-benzofuran-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(1-benzothiophen-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(1-benzothiophen-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(3,5-difluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(3-carbonitrilethien-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(3-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(4-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-(furan-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 (1R,4R,5R)-3-furan-3-yl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 3-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]benzoic acid
-
 Helicobacter pylori

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
4.2.1.10 3-dehydroquinate Helicobacter pylori
-
 3-dehydroshikimate + H2O
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
4.2.1.10 Helicobacter pylori Q48255
-
-

Purification (Commentary)

EC Number Purification (Comment) Organism
4.2.1.10 using a Q Sepharose, a phenyl Sepharose, a hydroxyapatite and a Sephacryl S300 column Helicobacter pylori

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
4.2.1.10 3-dehydroquinate
-
 Helicobacter pylori 3-dehydroshikimate + H2O
-
 ?

Synonyms

EC Number Synonyms Comment Organism
4.2.1.10 dehydroquinase
-
 Helicobacter pylori

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
4.2.1.10 25
-
 activity assay Helicobacter pylori

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
4.2.1.10 7.2
-
 activity assay Helicobacter pylori

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
4.2.1.10 0.00054
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(thien-2-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.001
-
 (1R,4R,5R)-3-(furan-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.001
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0018
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-thiophen-3-ylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0036
-
 (1R,4R,5R)-3-(1-benzothiophen-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0037
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-naphthalen-2-ylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0046
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-bromothien-2-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.00485
-
 (1R,4R,5R)-3-furan-3-yl-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0068
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(4-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0071
-
 (1R,4R,5R)-3-(1-benzofuran-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0074
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-phenylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0081
-
 (1R,4R,5R)-3-(1-benzothiophen-6-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0084
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[4-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0094
-
 (1R,4R,5R)-3-(3-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.011
-
 (1R,4R,5R)-3-(4-fluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0142
-
 (1R,4R,5R)-3-(1-benzofuran-5-yl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0205
-
 (1R,4R,5R)-3-(3,5-difluorophenyl)-1,4,5-trihydroxycyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.0384
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.056
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-pyridin-3-ylcyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.063
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(1H-1,2,3-triazol-4-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.11
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrothien-3-yl)cyclohex-2-en-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.128
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(3-hydroxyphenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.139
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-[3-(trifluoromethyl)phenyl]cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.141
-
 (1R,4R,5R)-1,4,5-trihydroxy-3-(2-nitrophenyl)cyclohex-2-ene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.15
-
 3-[(3R,5R,6R)-3-carboxy-3,5,6-trihydroxycyclohex-1-en-1-yl]benzoic acid
-
 Helicobacter pylori
4.2.1.10 0.37
-
 (1R,4R,5R)-1,4,5-trihydroxy-2-cyclohexene-1-carboxylic acid
-
 Helicobacter pylori
4.2.1.10 0.4
-
 (1R,4R,5R)-3-(3-carbonitrilethien-2-yl)-1,4,5-trihydroxycyclohex-2-en-1-carboxylic acid larger than 0.400 mM Helicobacter pylori