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Literature summary for 4.2.1.10 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
Search for more literature for 4.2.1.10

Application

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

Cloned(Commentary)

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

Inhibitors

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

Natural Substrates/ Products (Substrates)

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

Organism

Organism UniProt Comment Textmining
Helicobacter pylori Q48255
-
-

Purification (Commentary)

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

Substrates and Products (Substrate)

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

Synonyms

Synonyms Comment Organism
dehydroquinase
-
 Helicobacter pylori

Temperature Optimum [°C]

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

pH Optimum

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

Ki Value [mM]

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