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Literature summary extracted from

  • Hubrich, F.; Juneja, P.; Mueller, M.; Diederichs, K.; Welte, W.; Andexer, J.N.
    Chorismatase mechanisms reveal fundamentally different types of reaction in a single conserved protein fold (2015), J. Am. Chem. Soc., 137, 11032-11037 .
    View publication on PubMed

Protein Variants

EC Number Protein Variants Comment Organism
4.1.3.45 C327A the mutation leads to decreased activity (6%) compared to the wild type enzyme and results in a complete loss of product selectivity Streptomyces hygroscopicus
4.1.3.45 C327A the Hyg5 mutant shows 6% decreased activity compared to the wild-type, and results in a complete loss of product selectivity. The FkbO product (4R,5R)-4,5-dihydroxycyclohexa-1(6),2-diene-1-carboxylate as well as the XanB2 product 4-hydroxybenzoate are produced Streptomyces hygroscopicus
4.1.3.45 C327A/G240A the Hyg5 double mutant shows the same behavior as the single mutants, but along with a more dramatic loss of activity Streptomyces hygroscopicus
4.1.3.45 G240A the mutation leads to decreased activity (55%) compared to the wild type enzyme and results in a complete loss of product selectivity Streptomyces hygroscopicus
4.1.3.45 G240A the Hyg5 mutant shows 55% decreased activity compared to the wild-type, and results in a complete loss of product selectivity. The FkbO product (4R,5R)-4,5-dihydroxycyclohexa-1(6),2-diene-1-carboxylate as well as the XanB2 product 4-hydroxybenzoate are produced Streptomyces hygroscopicus

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.3.2.13 3-(2-carboxyethyl) benzoate
-
 Streptomyces hygroscopicus subsp. ascomyceticus
4.1.3.45 3-(2-carboxyethyl) benzoate
-
 Streptomyces hygroscopicus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.3.2.13 chorismate + H2O Streptomyces hygroscopicus subsp. ascomyceticus
-
 3,4-trans-dihydroxy-cyclohexa-1,5-diene-1-carboxylate
-
 ?
4.1.3.45 chorismate Streptomyces hygroscopicus
-
 3-hydroxybenzoate + pyruvate
-
 ?
4.1.3.45 chorismate Streptomyces hygroscopicus
-
 3-hydroxybenzoate + pyruvate
-
 ir

Organism

EC Number Organism UniProt Comment Textmining
3.3.2.13 Streptomyces hygroscopicus subsp. ascomyceticus Q9KID9
-
-
4.1.3.45 Streptomyces hygroscopicus O30478
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
3.3.2.13 chorismate + H2O = (4R,5R)-4,5-dihydroxycyclohexa-1(6),2-diene-1-carboxylate + pyruvate for the CH-FkbO subfamily, an isochorismatase-like hydrolysis mechanism is suggested where the acidic active site residue E338FkbO initially protonates the C3' of chorismate. This resulting carbocation intermediate is nucleophilically attacked by (activated) water leading to the formation of an unstable tetrahedral intermediate (hemiketal), which decomposes spontaneously into the products 3,4-trans-dihydroxy-cyclohexa-1,5-dienecarboxylate and pyruvate. Hydrolysis reaction mechanism analysis, overview Streptomyces hygroscopicus subsp. ascomyceticus
a
4.1.3.45 chorismate = 3-hydroxybenzoate + pyruvate a hydrolysis-elimination mechanism for CH-Hyg5 is observed. No external oxygen is incorporated into the Hyg5 products indicated an intramolecular mechanism for the Hyg5 reaction. A pericyclic mechanism, as described for chorismate-converting enzymes producing the 2- and 4-regioisomeric hydroxybenzoates, can also be ruled out due to the position of the hydroxyl group in 3-hydroxybenzoate. Arene oxide reaction mechansim analysis, overview Streptomyces hygroscopicus
a

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.3.2.13 chorismate + H2O
-
 Streptomyces hygroscopicus subsp. ascomyceticus 3,4-trans-dihydroxy-cyclohexa-1,5-diene-1-carboxylate
-
 ?
4.1.3.45 chorismate
-
 Streptomyces hygroscopicus 3-hydroxybenzoate + pyruvate
-
 ?
4.1.3.45 chorismate
-
 Streptomyces hygroscopicus 3-hydroxybenzoate + pyruvate
-
 ir
4.1.3.45 additional information no activity with 3,4-trans-dihydroxy-cyclohexa-1,5-diene-1-carboxylate and enoyl benzoate by enzyme Hyg5 Streptomyces hygroscopicus ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.3.2.13 CH-fkbo
-
 Streptomyces hygroscopicus subsp. ascomyceticus
3.3.2.13 chorismatases/chorismate hydrolase
-
 Streptomyces hygroscopicus subsp. ascomyceticus
3.3.2.13 fkbO
-
 Streptomyces hygroscopicus subsp. ascomyceticus
4.1.3.45 3-hydroxybenzoate synthase
-
 Streptomyces hygroscopicus
4.1.3.45 CH-Hyg5
-
 Streptomyces hygroscopicus
4.1.3.45 chorismatase
-
 Streptomyces hygroscopicus
4.1.3.45 chorismatase/3-hydroxybenzoate synthase
-
 Streptomyces hygroscopicus
4.1.3.45 hyg5
-
 Streptomyces hygroscopicus

General Information

EC Number General Information Comment Organism
3.3.2.13 evolution three subfamilies of chorismatases are described that convert chorismate into different (dihydro-)benzoate derivatives (CH-FkbO, CH-Hyg5, and CH-XanB2). The CH-FkbO and CH-Hyg5 subfamilies share the same protein fold, but employ fundamentally different reaction mechanisms, comparisons of the reaction mechanism of CH-FkbO and CH-Hyg5 and structure-function analysis, overview Streptomyces hygroscopicus subsp. ascomyceticus
4.1.3.45 evolution three subfamilies of chorismatases are described that convert chorismate into different (dihydro-)benzoate derivatives (CH-FkbO, CH-Hyg5, and CH-XanB2). The CH-FkbO and CH-Hyg5 subfamilies share the same protein fold, but employ fundamentally different reaction mechanisms, comparisons of the reaction mechanism of CH-FkbO and CH-Hyg5, and structure-function analysis, overview Streptomyces hygroscopicus
4.1.3.45 additional information involvement of residue C327 in directing the selectivity of product formation is underlined by the crystal structure of the mutant Hyg5 C327S with the product 3-hydroxybenzoate Streptomyces hygroscopicus