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Literature summary extracted from

  • Peon, A.; Otero, J.M.; Tizon, L.; Prazeres, V.F.; Llamas-Saiz, A.L.; Fox, G.C.; van Raaij, M.J.; Lamb, H.; Hawkins, A.R.; Gago, F.; Castedo, L.; Gonzalez-Bello, C.
    Understanding the key factors that control the inhibition of type II dehydroquinase by (2R)-2-benzyl-3-dehydroquinic acids (2010), ChemMedChem, 5, 1726-1733.
    View publication on PubMed

Crystallization (Commentary)

EC Number Crystallization (Comment) Organism
4.2.1.10 DHQ2 in complex with (2R)-2-p-methoxybenzyl-3-dehydroquinic acid, sitting drop vapour diffusion method, 20 mg/ml protein in 50 mM Tris-HCl, pH 7.5, 1 mM 2-mercaptoethanol, 1 mM EDTA, and 200 mM NaCl, with addition of (2R)-2-p-methoxybenzyl-3-dehydroquinic acid at 0.25 M in methanol and added at a ratio of 1:20 v/v, mixing of 0.002 ml protein solution with 0.002 ml reservoir solution containing 31% w/v PEG 4000 and 0.1 M sodium citrate, pH 5.0, and equilibation against 0.15 ml reservoir solution, room temperature, X-ray diffraction structure determination and analysis at 2.4-2.5 A resolution, modelling Helicobacter pylori
4.2.1.10 DHQ2 in complex with (2R)-2-p-methoxybenzyl-3-dehydroquinic acid, sitting drop vapour diffusion method, 20 mg/ml protein in 50 mM Tris-HCl, pH 7.5, 1 mM 2-mercaptoethanol, 1 mM EDTA, and 200 mM NaCl, with addition of (2R)-2-p-methoxybenzyl-3-dehydroquinic acid at 0.25 M in methanol and added at a ratio of 1:20 v/v, mixing of 0.002 ml protein solution with 0.002 ml reservoir solution containing 32% v/v 2-methyl-2,4-pentanediol, 0.3 M ammonium sulfate and 0.1 M HEPES, pH 7.5, and equilibation against 0.15 ml reservoir solution, room temperature, X-ray diffraction structure determination and analysis at 2.4-2.5 A resolution, modelling Mycobacterium tuberculosis

Inhibitors

EC Number Inhibitors Comment Organism Structure
4.2.1.10 (2R)-2-p-methoxybenzyl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2 Helicobacter pylori
4.2.1.10 (2R)-2-p-methoxybenzyl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis
4.2.1.10 (2R)-2-p-methylbenzyl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2 Helicobacter pylori
4.2.1.10 (2R)-2-p-methylbenzyl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis
4.2.1.10 (2R)-2-pentafluoro-benzyl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2 Helicobacter pylori
4.2.1.10 (2R)-2-pentafluoro-benzyl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis
4.2.1.10 benzo[b]thiophen-5-yl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2 Helicobacter pylori
4.2.1.10 benzo[b]thiophen-5-yl-3-dehydroquinic acid a reversible, competitive inhibitor of DHQ2, pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis
4.2.1.10 additional information binding mechanism of (2R)-2-benzyl-3-dehydroquinic acids, molecular dynamics simulations, overview Helicobacter pylori
4.2.1.10 additional information binding mechanism of (2R)-2-benzyl-3-dehydroquinic acids, molecular dynamics simulations, overview Mycobacterium tuberculosis

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 Mycobacterium tuberculosis
-
3-dehydroshikimate + H2O
-
?
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
-
-
4.2.1.10 Mycobacterium tuberculosis
-
-
-

Substrates and Products (Substrate)

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

Synonyms

EC Number Synonyms Comment Organism
4.2.1.10 DHQ2
-
Mycobacterium tuberculosis
4.2.1.10 DHQ2
-
Helicobacter pylori
4.2.1.10 Type II dehydroquinase
-
Mycobacterium tuberculosis
4.2.1.10 Type II dehydroquinase
-
Helicobacter pylori

IC50 Value

EC Number IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
4.2.1.10 0.000026
-
pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis (2R)-2-p-methoxybenzyl-3-dehydroquinic acid
4.2.1.10 0.000028
-
pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis benzo[b]thiophen-5-yl-3-dehydroquinic acid
4.2.1.10 0.000047
-
pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis (2R)-2-pentafluoro-benzyl-3-dehydroquinic acid
4.2.1.10 0.000089
-
pH not specified in the publication, temperature not specified in the publication Mycobacterium tuberculosis (2R)-2-p-methylbenzyl-3-dehydroquinic acid
4.2.1.10 0.00016
-
pH and temperature not specified in the publication Helicobacter pylori benzo[b]thiophen-5-yl-3-dehydroquinic acid
4.2.1.10 0.00017
-
pH and temperature not specified in the publication Helicobacter pylori (2R)-2-p-methoxybenzyl-3-dehydroquinic acid
4.2.1.10 0.00025
-
pH and temperature not specified in the publication Helicobacter pylori (2R)-2-p-methylbenzyl-3-dehydroquinic acid
4.2.1.10 0.0026
-
pH and temperature not specified in the publication Helicobacter pylori (2R)-2-pentafluoro-benzyl-3-dehydroquinic acid

General Information

EC Number General Information Comment Organism
4.2.1.10 evolution There are two distinct dehydroquinases, designated as type I DHQ1, and type II DHQ2, which have different biochemical and biophysical properties and exhibit little sequence similarity. Both subtypes catalyze the same overall reaction through independent mechanisms and with opposite stereochemistry. Type I DHQ occurs in Escherichia coli and Salmonella typhimurium, type II DHQ in Mycobacterium tuberculosis, Streptomyces coelicolor and Helicobacter pylori Mycobacterium tuberculosis
4.2.1.10 evolution There are two distinct dehydroquinases, designated as type I DHQ1, and type II DHQ2, which have different biochemical and biophysical properties and exhibit little sequence similarity. Both subtypes catalyze the same overall reaction through independent mechanisms and with opposite stereochemistry. Type I DHQ occurs in Escherichia coli and Salmonella typhimurium, type II DHQ in Mycobacterium tuberculosis, Streptomyces coelicolor and Helicobacter pylori Helicobacter pylori
4.2.1.10 metabolism dehydroquinase is the third enzyme in the shikimic acid pathway and catalyzes the reversible dehydration of 3-dehydroquinic acid to form 3-dehydroshikimic acid Mycobacterium tuberculosis
4.2.1.10 metabolism dehydroquinase is the third enzyme in the shikimic acid pathway and catalyzes the reversible dehydration of 3-dehydroquinic acid to form 3-dehydroshikimic acid Helicobacter pylori