4.2.99.21: isochorismate lyase
This is an abbreviated version!
For detailed information about isochorismate lyase, go to the full flat file.
Word Map on EC 4.2.99.21
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4.2.99.21
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siderophore
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pericyclic
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chorismate-utilizing
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prephenate
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2,3-dihydroxybenzoate
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anthranilate
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mg2+-dependent
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enterobactin
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drug development
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agriculture
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biotechnology
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synthesis
- 4.2.99.21
-
siderophore
-
pericyclic
-
chorismate-utilizing
- prephenate
- 2,3-dihydroxybenzoate
- anthranilate
-
mg2+-dependent
- enterobactin
- drug development
- agriculture
- biotechnology
- synthesis
Reaction
Synonyms
pyochelin biosynthetic protein PchB, IPL, Irp9, isochorismate pyruvate lyase, isochorismate-pyruvate lyase, MbtI, PchA, PchB, PRXR1, salicylate biosynthesis protein pchB, salicylate synthase
ECTree
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Reaction
Reaction on EC 4.2.99.21 - isochorismate lyase
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isochorismate = salicylate + pyruvate
[1,5]-sigmatropic reaction mechanism that invokes electrostatic catalysis in analogy to the [3,3]-pericyclic rearrangement of chorismate in chorismate mutase
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isochorismate = salicylate + pyruvate
a reactive substrate conformation is formed upon loop closure of the active site and ordering of the loop contributes to the entropic penalty for converting the enzyme substrate complex to the transition state. The thermodynamic parameters of the physiological lyase activity of PchB show that the reaction is clearly enthalpically driven, and has a very large entropic penalty of 24.3 cal/(mol K), which is more than 1.5-fold greater than that of the uncatalyzed reaction of 15.77 cal/(mol K)
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isochorismate = salicylate + pyruvate
kinetic mechanism and transition state of the elimination reaction, overview
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isochorismate = salicylate + pyruvate
reaction mechanism with catalytic residue Lys42, modeling, overview
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isochorismate = salicylate + pyruvate
reaction mechanism, the IPL reaction is a concerted but asynchronous hydrogen transfer, by a proposed [1,5]-sigmatropic reaction mechanism with a pericyclic transition state, quantum mechanical/molecular-mechanical calculations and simulations, overview
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isochorismate = salicylate + pyruvate
the enzyme achieves catalysis of both pericyclic reactions, isochorismate-pyruvate lyase and chorismate-pyruvate lyase, EC 4.1.3.40, in part by the stabilization of reactive conformations and in part by electrostatic transition-state stabilization. Both, substrate organization and electrostatic transition state stabilization, contribute to catalysis
isochorismate = salicylate + pyruvate
the lysine42 residue is required in a specific conformation to stabilize the transition state
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isochorismate = salicylate + pyruvate
overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate
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isochorismate = salicylate + pyruvate
overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate
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isochorismate = salicylate + pyruvate
overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate
isochorismate = salicylate + pyruvate
overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate. In the second reaction, pyruvate is eliminated through an intramolecular [3,3]-sigmatropic rearrangement, formerly a retro-Ene reaction, to afford salicylic acid via bicyclic transition state TS2
isochorismate = salicylate + pyruvate
overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate
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isochorismate = salicylate + pyruvate
overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate. In the second reaction, pyruvate is eliminated through an intramolecular [3,3]-sigmatropic rearrangement, formerly a retro-Ene reaction, to afford salicylic acid via bicyclic transition state TS2
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