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Literature summary for 5.3.3.1 extracted from

  • Kraut, D.A.; Sigala, P.A.; Pybus, B.; Liu, C.W.; Ringe, D.; Petsko, G.A.; Herschlag, D.
    Testing electrostatic complementarity in enzyme catalysis: hydrogen bonding in the ketosteroid isomerase oxyanion hole (2006), PLoS Biol., 4, 501-519.
No PubMed abstract available

Crystallization (Commentary)

Crystallization (Comment) Organism
enzyme mutant D40N bound to phenolate, X-ray diffraction structure determination and analysis at 1.25 A resolution Pseudomonas putida

Protein Variants

Protein Variants Comment Organism
D103A site-directed mutagenesis of the catalytic residue, the mutant shows 5000fold reduced activity compared tot he wild-type enzyme Comamonas testosteroni
D40N site-directed mutagenesis, the mutation mimics the protonated aspartate found in the intermediate and equilenin complexes and leads to tighter binding of phenolate and other intermediate analogs Pseudomonas putida
D40N site-directed mutagenesis, the mutation mimics the protonated aspartate found in the intermediate and equilenin complexes and leads to tighter binding of phenolate and other intermediate analogs Comamonas testosteroni
Y16F site-directed mutagenesis of the catalytic residue, the mutant shows 50000fold reduced activity compared tot he wild-type enzyme Comamonas testosteroni

KM Value [mM]

KM Value [mM] KM Value Maximum [mM] Substrate Comment Organism Structure
additional information
-
additional information kinetics Pseudomonas putida
additional information
-
additional information kinetics Comamonas testosteroni

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
a 3-oxo-DELTA5-steroid Pseudomonas putida
-
a 3-oxo-DELTA4-steroid
-
r
a 3-oxo-DELTA5-steroid Comamonas testosteroni
-
a 3-oxo-DELTA4-steroid
-
r

Organism

Organism UniProt Comment Textmining
Comamonas testosteroni
-
-
-
Pseudomonas putida
-
-
-

Reaction

Reaction Comment Organism Reaction ID
a 3-oxo-DELTA5-steroid = a 3-oxo-DELTA4-steroid catalytic mechanism, phenolate binding to the oxyanion hole of ketosteroid isomerase via hydrogen bonding, electrostatic contributions and geometric and electrostatic changes, overview, the KSI reaction involves changes in both geometry and charge distribution as the reaction proceeds from its ground state to its intermediate Pseudomonas putida
a 3-oxo-DELTA5-steroid = a 3-oxo-DELTA4-steroid catalytic mechanism, phenolate binding to the oxyanion hole of ketosteroid isomerase via hydrogen bonding, electrostatic contributions and geometric and electrostatic changes, overview, the KSI reaction involves changes in both geometry and charge distribution as the reaction proceeds from its ground state to its intermediate, Tyr16 and Asp103 are important in catalysis Comamonas testosteroni

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
a 3-oxo-DELTA5-steroid
-
Pseudomonas putida a 3-oxo-DELTA4-steroid
-
r
a 3-oxo-DELTA5-steroid
-
Comamonas testosteroni a 3-oxo-DELTA4-steroid
-
r
a 3-oxo-DELTA5-steroid phenolates binding to the oxyanion hole of the enzyme via electrostatic interactions, different binding of transition state analogue and substrate, hydrogen bonds shorten with increasing charge localization, overview Comamonas testosteroni a 3-oxo-DELTA4-steroid
-
r
a 3-oxo-DELTA5-steroid phenolates binding to the oxyanion hole of the enzyme via hydrogen bonding, different binding of transition state analogue and substrate, hydrogen bonds shorten with increasing charge localization, overview Pseudomonas putida a 3-oxo-DELTA4-steroid
-
r
additional information equilenin geometrically and electrostatically resembles the dienolate reaction intermediate and transition state, binding structure to enzyme mutant D40N, overview Comamonas testosteroni ?
-
?

Synonyms

Synonyms Comment Organism
ketosteroid isomerase
-
Pseudomonas putida
ketosteroid isomerase
-
Comamonas testosteroni
KSI
-
Pseudomonas putida
KSI
-
Comamonas testosteroni