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Synonyms
ics, isochorismate synthase, amonabactin, salicylate synthase, isochorismate synthase 1, eds16, atics1, isochorismate hydroxymutase, atics2, menaquinone-specific isochorismate synthase,
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chorismate = isochorismate
chorismate = isochorismate
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chorismate = isochorismate
K90 is the base that activates water for nucleophilic attack at the chorismate C2 carbon
chorismate = isochorismate
general acid-general base catalysis with a lysine as the base and a glutamic acid as the acid, in reverse protonation states and with a conformational or binding step as the slow step
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chorismate = isochorismate
isochorismate synthase (IS) performs a 1,5-displacement mechanism during the chorismate conversion to intermediates through the use of a nucleophile, which is water in the case of IS, but might also be possible with ammonia. The hydroxyl group in the isochorismate is generated from water and not through an intramolecular rearrangement
chorismate = isochorismate
isochorismate synthase performs a 1,5-displacement mechanism during the chorismate conversion to intermediates through the use of a nucleophile, which is water in the case of isochorismate synthase, but might also be possible with ammonia. The hydroxyl group in the isochorismate is generated from water and not through an intramolecular rearrangement
chorismate = isochorismate
overall reaction, salicylate sythase converts chorismate into salicylate via an isochorismate intermediate. The isochorismatase activity of bifunctional enzyme MbtI requires Lys205, which nucleophilically activates a water molecule for attack on chorismate at C-6 and Glu252 that polarizes the C-4 hydroxyl-leaving group
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additional information
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Chorismate
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two different isochorismate mutases, one is involved in the biosynthesis of the respiratory chain component menaquinone, MedF, and the other is involved in the synthesis of siderophore 2,3-dihydroxybenzoate, DhbC
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Chorismate
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the first enzyme involved in the biosynthesis of the powerful iron-chelating agent enterobactin
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Chorismate
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first committed step in the biosynthesis of menaquinone
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Chorismate
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enzyme catalyzes the pivotal step in enterobactin and menaquinone biosynthesis
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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reaction operates near equilibrium, equilibrium constant is 0.89. Enzyme does not convert chorismate directly to salicylic acid
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r
Chorismate
Isochorismate
alternative pathway to produce salicyl acid in response to pathogens
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Chorismate
Isochorismate
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involved in biosynthesis of salicylic acid
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Chorismate
Isochorismate
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Chorismate
Isochorismate
Q81QQ0
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r
Chorismate
Isochorismate
Q81QQ0
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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ir
Chorismate
Isochorismate
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Chorismate
Isochorismate
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not reversible, isochorismate synthase involved in enterobactin biosynthesis, MenF
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Chorismate
Isochorismate
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r, isochorismate synthase involved in menaquinone biosynthesis, EntC
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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r
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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r
Chorismate
Isochorismate
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r
Chorismate
Isochorismate
first enzyme of pyochelin biosynthesis
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r
Chorismate
Isochorismate
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Chorismate
Isochorismate
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r
Chorismate
Isochorismate
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r
isochorismate
chorismate
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r
isochorismate
chorismate
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r
isochorismate
chorismate
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r
additional information
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ICS2 participates in the synthesis of SA, but in limited amounts that become clearly detectable only when ICS1 is lacking
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additional information
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isozyme ICS1 does not act as isochorismate pyruvate lyase (IPL, EC 4.2.99.21) and bifunctional salicylate synthase, it does not convert chorismate into salicylate
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additional information
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isozyme ICS1 does not act as isochorismate pyruvate lyase (IPL, EC 4.2.99.21) and bifunctional salicylate synthase, it does not convert chorismate into salicylate
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additional information
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isozyme ICS1 does not act as isochorismate pyruvate lyase (IPL, EC 4.2.99.21) and bifunctional salicylate synthase, it does not convert chorismate into salicylate
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additional information
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isozyme ICS2 does not act as isochorismate pyruvate lyase (IPL, EC 4.2.99.21) and bifunctional salicylate synthase, it does not convert chorismate into salicylate
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additional information
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isozyme ICS2 does not act as isochorismate pyruvate lyase (IPL, EC 4.2.99.21) and bifunctional salicylate synthase, it does not convert chorismate into salicylate
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additional information
?
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isozyme ICS2 does not act as isochorismate pyruvate lyase (IPL, EC 4.2.99.21) and bifunctional salicylate synthase, it does not convert chorismate into salicylate
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additional information
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the enzyme is essential for siderohore biosynthesis, first step in salicylate production
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additional information
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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
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additional information
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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
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additional information
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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
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additional information
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ICS enzyme is also required for salicylic acid biosynthesis
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additional information
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ICS enzyme is also required for salicylic acid biosynthesis
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additional information
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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
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additional information
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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
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
additional information
?
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the enzyme is essential for siderohore biosynthesis, first step in salicylate production
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Chorismate
?
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two different isochorismate mutases, one is involved in the biosynthesis of the respiratory chain component menaquinone, MedF, and the other is involved in the synthesis of siderophore 2,3-dihydroxybenzoate, DhbC
-
-
?
Chorismate
?
-
the first enzyme involved in the biosynthesis of the powerful iron-chelating agent enterobactin
-
-
?
Chorismate
?
-
first committed step in the biosynthesis of menaquinone
-
-
?
Chorismate
?
-
enzyme catalyzes the pivotal step in enterobactin and menaquinone biosynthesis
-
-
?
Chorismate
Isochorismate
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?
Chorismate
Isochorismate
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r
Chorismate
Isochorismate
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r
Chorismate
Isochorismate
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r
Chorismate
Isochorismate
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r
Chorismate
Isochorismate
alternative pathway to produce salicyl acid in response to pathogens
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?
Chorismate
Isochorismate
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involved in biosynthesis of salicylic acid
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?
Chorismate
Isochorismate
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r
Chorismate
Isochorismate
Q81QQ0
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r
Chorismate
Isochorismate
Q81QQ0
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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Chorismate
Isochorismate
first enzyme of pyochelin biosynthesis
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Chorismate
Isochorismate
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Chorismate
Isochorismate
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isochorismate
chorismate
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isochorismate
chorismate
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r
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Mg2+
absolutely required
Mg2+
dependent on, Km for ICS1 is 0.942 mM
Mg2+
dependent on, Km for ICS2 is 0.55 mM
Mg2+
Q81QQ0
Mg2+-dependent catalytic mechanism
Mg2+
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sharp increase in activity, optimal concentration: 1 mM, inhibition above 1 mM
Mg2+
required for catalysis
Mg2+
the enzyme contains Mg2+
Mg2+
strongly dependent on, magnesium ions interact with chorismate in the active site, forming a magnesium-coordinated transition state during the reaction
Mg2+
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absolute requirement
Mg2+
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optimal concentration for soluble enzyme: 5-20 mM. Optimal concentration for enzyme immobilized on CNBr-Sepharose or alkylamine glass: 2.5-5 mM. Activity of the soluble enzyme without Mg2+ is 5.5% of the activity without Mg2+
Mg2+
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absolute requirement
Mg2+
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stimulates, optimal concentration: 2-5 mM
Mg2+
strictly required for activity
Mg2+
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required, chelated by residues D310, E313, and H348
Mg2+
strongly dependent on, magnesium ions interact with chorismate in the active site, forming a magnesium-coordinated transition state during the reaction
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(4R,5R)-4-hydroxy-5-(1-carboxyvinyloxy)-cyclohex-1-ene carboxylate
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(4R,5R)-4-hydroxy-5-carboxymethoxy-cyclohex-1-enecarboxylate
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(4R,5R)-5-(2-carboxy-allyloxy)-4-hydroxy-cyclohex-1-enecarboxylate
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(4R,5R)-5-(carboxymethoxy)-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
(4R,5R)-5-[(1R)-1-carboxyethoxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R)-5-[(1S)-1-carboxyethoxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R)-5-[(2-carboxyprop-2-en-1-yl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R,6S)-6-amino-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
(4R,5R,6S)-6-ammonio-5-[(1-carboxylatoethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylate
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(4R,5R,7R)-5-(1-carboxy-ethoxy)-4-hydroxy-cyclohex-1-enecarboxylate
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(4R,5R,7S)-5-(1-carboxy-ethoxy)-4-hydroxy-cyclohex-1-enecarboxylate
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(4R,5S,6R)-4-amino-5-(2-carboxyethyl)-6-hydroxycyclohex-1-ene carboxylic acid
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transition-state inhibitor
(4R,5S,6R)-4-amino-5-(2-carboxyethyl)-6-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5S,6S)-4-amino-5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohex-1-ene-1-carboxylic acid
(4R,5S,6S)-4-ammonio-5-[(1-carboxylatoethenyl)oxy]-6-hydroxycyclohex-1-ene-1-carboxylate
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(4R,5S,6S)-5-[(1-carboxyethenyl)oxy]-4,6-dihydroxycyclohex-1-ene-1-carboxylic acid
(4R,5S,6S)-5-[(1-carboxylatoethenyl)oxy]-4,6-dihydroxycyclohex-1-ene-1-carboxylate
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(E)-1-(tert-butyldimethylsilyloxy)-1,3-butadiene
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3-[[(1Z)-1-carboxyprop-1-en-1-yl]oxy]-2-hydroxybenzoic acid
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benzimidazole-2-thione
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noncompetitive inhibitor with
oseltamivir
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i.e. Tamiflu
salicylic acid
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treatment of plants suppresses the enhancement of enzyme expression by O3
(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
inhibition of isochorismate synthase activity and salicylate synthase activity
(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R)-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R,6S)-6-amino-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5R,6S)-6-amino-5-[(1-carboxyethenyl)oxy]-4-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5S,6S)-4-amino-5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5S,6S)-4-amino-5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5S,6S)-5-[(1-carboxyethenyl)oxy]-4,6-dihydroxycyclohex-1-ene-1-carboxylic acid
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(4R,5S,6S)-5-[(1-carboxyethenyl)oxy]-4,6-dihydroxycyclohex-1-ene-1-carboxylic acid
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additional information
inhibitor structure-function relationship and molecular docking
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additional information
inhibitor structure-function realtionship and molecular docking
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additional information
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design, synthesis and biochemical evaluation of inhibitor 4 based on the putative transition-state (TS) for the isochorismatase partial reaction of MbtI. The inhibitor mimics the hypothesized charge build-up at C-4 of chorismate in the TS as well as C-O bond-formation at C-6. Another important design element of the inhibitor is replacement of the labile pyruvate side-chain in chorismate with a stable C-linked propionate isostere. Development of a stereocontrolled synthesis of the highly functionalized cyclohexene inhibitor that features an asymmetric aldol reaction using a titanium enolate, diastereoselective Grignard addition to a tert-butanesulfinyl aldimine, and ring closing olefin metathesis as key steps
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additional information
inhibitor structure-function relationship and molecular docking
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additional information
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inhibitor structure-function relationship and molecular docking
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additional information
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inhibitor structure-function relationship and molecular docking
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5.4.4.2 isochorismate synthase
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