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pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
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pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
pyruvate binds to the enzyme first by forming a Schiff base with the epsilon-amino group of Lys161. After release of the first water molecule L-aspartate-4-semialdehyde binds to the active site and the condensation reaction to form 2,3-dihydrodipicolinate takes place
-
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
the reaction is initiated by an nucleophilic attack of the epsilon-amino group of active site lysine to the C2 atom of pyruvate with subsequent imine formation. Tautomerization of the imine to the enamine creates the nucleophile necessary for the attack of the aldehyde group of L-aspartate semialdehyde. Cyclization of the substrate coupled with transamination leads to stepwise detachment from the active site
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pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
ping-pong mechanism, pyruvate binds as a Schiff base to Lys161. After aldol reaction with L-aspartate-4-semialdehyde and transamination the product is released
-
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
ping-pong kinetic and catalytic mechanism involves a catalytic triad which consists of Tyr133, Thr44, and Tyr107, overview
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
reaction mechanism including Schiff base formation, tautomerization, and cyclization, overview
-
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
ping-pong kinetic reaction mechanism
-
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
ping-pong mechanism, in which pyruvate binds as a Schiff base to an active-site lysine residue (Lys162 in Agrobacterium tumefaciens)
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
reaction steps, overview
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
the enzyme-catalyzed reaction is initiated by condensation of pyruvate with an active site lysine residue (Lys161 in Escherichia coli DHDPS) forming a Schiff base, ping-pong kinetic reaction mechanism via enamine intermediate, overview
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
the reaction proceeds via a ping-pong kinetic mechanism in which pyruvate binds and forms a Schiff base to an active-site lysine residue (Lys184 in Vitis vinifera enzyme). L-aspartate-4-semialdehyde then reacts with the resultant enamine and following cyclization forms the product (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate
pyruvate + L-aspartate-4-semialdehyde = (2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
ping-pong mechanism, in which pyruvate binds as a Schiff base to an active-site lysine residue (Lys162 in Agrobacterium tumefaciens)
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(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
L-aspartate 4-semialdehyde + pyruvate
(S)-2,3-dihydropyridine-2,6-dicarboxylate + 2 H2O
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
L-aspartate-4-semialdehyde + pyruvate
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
pyruvate + (R,S)-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
pyruvate + DL-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
-
-
-
-
?
pyruvate + L-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
pyruvate + L-aspartate-4-semialdehyde
2,3-dihydrodipicolinate + ?
additional information
?
-
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
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?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
characterization of thermostable enzyme features, substrate specificity tested, activity measurements at elevated temperature of 60°C
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-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
branch point reaction in the biosynthesis of lysine
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?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
first step in the biosynthesis of lysine, overview
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
biosynthesis of (S)-lysine and meso-diaminopimelate
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?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
diketopimelic acid derivatives designed as mimics of the acyclic enzyme-bound condensation product of (S)-aspartate 4-semialdehyde and pyruvate, inhibition analysis
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?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
reaction mechanism and active site analyzed, inhibition by the substrate analog beta-hydroxypyruvate
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?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
role of Tyr107 residue, located at the tight-dimer interface between two monomers, participates in a catalytic triad of residues during catalysis
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?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
first step in the biosynthesis of lysine, overview
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
biosynthesis of (S)-lysine and meso-diaminopimelate, compounds of bacterial cell walls
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-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
mechanistic insight into catalysis, structural features, evolution of quaternary structure
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-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
biosynthesis of (S)-lysine and meso-diaminopimelate, compounds of bacterial cell walls
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
mechanistic insight into catalysis, structural features, evolution of quaternary structure
-
-
?
(S)-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
catalyses the branch point in lysine biosynthesis
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-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
bi-bi ping-pong substrate model
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-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
bi-bi ping-pong substrate model
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
(S)-aspartate-4-semialdehyde binds cooperatively in the presence of (S)-lysine with an average cooperativity coefficient n = 1.3, and the cooperativity of binding increases at near-KM concentrations of pyruvate with an average cooperativity coefficient n = 1.0
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?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
the enzyme-catalyzed reaction is initiated by condensation of pyruvate with an active site Lys161 forming a Schiff base. Subsequent tautomerization to the enamine and aldol-type reaction with (S)-aspartate-4-semialdehyde then generates an acyclic enzyme-bound intermediate. Transimination of the acyclic intermediate yields the cyclic alcohol (4S)-4-hydroxy-2,3,4,5-tetrahydro-(2S)-dipicolinic acid, with simultaneous release of the active site lysine residue
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?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
?
(S)-aspartate-4-semialdehyde + pyruvate
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinic acid + H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
(S)-2,3-dihydropyridine-2,6-dicarboxylate + 2 H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
(S)-2,3-dihydropyridine-2,6-dicarboxylate + 2 H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
(S)-2,3-dihydropyridine-2,6-dicarboxylate + 2 H2O
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
(S)-2,3-dihydropyridine-2,6-dicarboxylate + 2 H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
Q81WN7
-
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?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
-
-
-
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?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
Q81WN7
active sites are similiar to Escherichia coli DHDPS
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?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
Q81WN7
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
-
active sites are similiar to Bacillus anthracis DHDPS
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
condensation reaction between both substrates via the formation of a Schiff base intermediate between pyruvate and the absolutely conserved active-site lysine. Although lysine 161 is important in the wild-type DHDPS-catalysed reaction, it is not absolutely essential for catalysis
-
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?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
pyruvate is a weak binder (0.023 mM) and L-aspartate 4-semialdehyde does not interact with the enzyme in the absence of a Schiff-base with pyruvate. Lys161 plays a crucial role in providing the thermodynamic force for the association of pyruvate with the DHDPS active site
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-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
slightly higher affinity for L-aspartate 4-semialdehyde and somewhat lower affinity for pyruvate than the Escherichia coli enzyme, whereby the catalytic activity is similar
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + 2 H2O
slightly higher affinity for L-aspartate 4-semialdehyde and somewhat lower affinity for pyruvate than the Escherichia coli enzyme, whereby the catalytic activity is similar
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-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
lysine insensitivity of dihydrodipicolinate synthase analyzed, catalytic lysine residue forms a Schiff base adduct with pyruvate, active site lysine residues (K176a, K176b)
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?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
branch poit of (S)-lysine biosynthesis
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
substrate protection and inhibition experiments
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
isothermal titration calorimetry (ITC) to study Schiff base formation between an enzyme and its substrate, pyruvate condenses with an active site lysine residue (Lys161 in MosA)
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?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
isothermal titration calorimetry (ITC) to study Schiff base formation between an enzyme and its substrate, pyruvate condenses with an active site lysine residue (Lys161 in MosA)
-
-
?
L-aspartate 4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
?
-
synthesis of the precursor of dipicolinic acid which plays a key role in bacterial sporulation process
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?
L-aspartate-4-semialdehyde + pyruvate
?
-
first enzyme in the meso-diaminopimelate and L-lysine branch of the aspartate pathway
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?
L-aspartate-4-semialdehyde + pyruvate
?
-
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?
L-aspartate-4-semialdehyde + pyruvate
?
-
biosynthesis of lysine via the diaminopimelate pathway
-
-
?
L-aspartate-4-semialdehyde + pyruvate
?
-
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
Cucurbita sp.
-
-
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?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
(4S)-4-hydroxy-2,3,4,5-terahydro-(2S)-dipicolinic acid is the initial but instable product
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
Phaseolus sp.
-
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?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
D-isomer inactive
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
L-aspartate-4-semialdehyde + pyruvate
dihydrodipicolinate + H2O
-
-
-
?
pyruvate + (R,S)-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
-
-
-
-
?
pyruvate + (R,S)-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
-
-
-
-
?
pyruvate + L-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
-
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?
pyruvate + L-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
the enzyme catalyzes a step of the diaminopimelate biosynthetic pathway of lysine
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?
pyruvate + L-aspartate-4-semialdehyde
(2S,4S)-4-hydroxy-2,3,4,5-tetrahydrodipicolinate + H2O
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4.3.3.7 4-hydroxy-tetrahydrodipicolinate synthase
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