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Literature summary for 4.2.99.21 extracted from

  • Liu, Z.; Liu, F.; Aldrich, C.C.
    Stereocontrolled synthesis of a potential transition-state inhibitor of the salicylate synthase MbtI from Mycobacterium tuberculosis (2015), J. Org. Chem., 80, 6545-6552 .
    View publication on PubMedView publication on EuropePMC
Search for more literature for 4.2.99.21

Application

Application Comment Organism
drug development enzyme MbtI represents an appealing target for development of inhibitors of mycobactin biosynthesis since it is structurally and biochemically characterized, has no human orthologues, and is conditionally essential under iron-deficient conditions. Inhibitors are designed against the isochorismatase activity of the enzyme (EC 5.4.4.2) Mycobacterium tuberculosis

Metals/Ions

Metals/Ions Comment Organism Structure
Mg2+ required Mycobacterium tuberculosis

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
isochorismate Mycobacterium tuberculosis
-
 salicylate + pyruvate
-
 ?
isochorismate Mycobacterium tuberculosis ATCC 25618
-
 salicylate + pyruvate
-
 ?

Organism

Organism UniProt Comment Textmining
Mycobacterium tuberculosis P9WFX1
-
-
Mycobacterium tuberculosis ATCC 25618 P9WFX1
-
-

Reaction

Reaction Comment Organism Reaction ID
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 Mycobacterium tuberculosis
a

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
isochorismate
-
 Mycobacterium tuberculosis salicylate + pyruvate
-
 ?
isochorismate
-
 Mycobacterium tuberculosis ATCC 25618 salicylate + pyruvate
-
 ?
additional information the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities Mycobacterium tuberculosis ?
-
 ?
additional information the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities Mycobacterium tuberculosis ATCC 25618 ?
-
 ?

Synonyms

Synonyms Comment Organism
MbtI
-
 Mycobacterium tuberculosis
salicylate synthase EC 5.4.4.2 and 4.2.99.21 Mycobacterium tuberculosis

General Information

General Information Comment Organism
metabolism the bifunctional salicylate synthase converts chorismate into salicylate through a two-step reaction, exhibiting both isochorismate synthase (EC 5.4.4.2) and isochorismate lyase (EC 4.2.99.21) activities Mycobacterium tuberculosis
physiological function mycobactins are small-molecule iron chelators (siderophores) produced by Mycobacterium tuberculosis (Mtb) for iron mobilization. Siderophores are small-molecule iron chelators that scavenge iron from host tissues and uptake of heme through a specialized heme receptor followed by heme degradation to release the iron. The bifunctional salicylate synthase MbtI catalyzes the first step of mycobactin biosynthesis through the conversion of the primary metabolite chorismate into salicylic acid via isochorismate Mycobacterium tuberculosis