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shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
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shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
active site structure, reaction and kinetic mechanisms
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shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
conserved residues Asp103 and Lys67 are important for catalysis in all three paralogues, kinetic mechanism of paralogue HI0607 and substrate binding site
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shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
active-site base is K92. After the binding of quinate and NAD+, the oxygen of the C3-OH of quinate forms a hydrogen bond to the side chain of the conserved T88 and K92 functions as the active-site base to remove the proton on the C3-OH. Simultaneously,a hydride is transferred from C3 of quinate to NAD+
shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
steady-state ordered bi-bi kinetic mechanism. The hydride transferred from NADPH and protons transferred from the solvent in the catalytic cycle are not significantly rate limiting in the overall reaction. Both hydride and proton transfers are concerted, and acid/base chemistry takes place in catalysis and substrate binding
shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
the active enzyme for dehydrogenation of shikimate contains a deprotonated K70 residue, a deprotonated D106, and a protonated Y216. The hydride transfer and the deprotonation of the 3-hydroxyl group of shikimate proceed in a concerted manner. K70 functions as a general base and becomes protonated in the dehydrogenation reaction. The proton is then transferred to the bulk solvent via the short proton-conducting wire. D106 plays a critical role in the transfer of the proton to the bulk solvent
shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
the pro-R hydrogen of the nicotinamide C4 is 3.35 A from the C3 of shikimate. The catalytic K385 and D423 residues are proximal to the C3-hydroxyl of shikimate, which is deprotonated in the oxidation reaction. The enzyme adopts a concave architecture that places the active sites in a face-to-face arrangement
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shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
catalytic mechanism, residue Lys69 plays a catalytic role and is not involved in substrate binding, overview
shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
the enzyme catalysis follows a sequential random mechanism, enzyme catalysis depends on acid-basic amino acids
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shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
steady-state ordered bi-bi kinetic mechanism. The hydride transferred from NADPH and protons transferred from the solvent in the catalytic cycle are not significantly rate limiting in the overall reaction. Both hydride and proton transfers are concerted, and acid/base chemistry takes place in catalysis and substrate binding
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shikimate + NADP+ = 3-dehydroshikimate + NADPH + H+
the enzyme catalysis follows a sequential random mechanism, enzyme catalysis depends on acid-basic amino acids
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3-dehydroquinate
3-dehydroshikimate + H2O
3-dehydroquinate + NADH + H+
quinate + NAD+
3-dehydroquinate + NADPH + H+
quinate + NADP+
3-dehydroshikimate + NAD(P)H + H+
shikimate + NAD(P)+
3-dehydroshikimate + NADH
shikimate + NAD+
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SDH reaction, very low activity with NAD+
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r
3-dehydroshikimate + NADH + H+
shikimate + NAD+
3-dehydroshikimate + NADP+
gallate + NADPH + H+
3-dehydroshikimate + NADPH
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3-dehydroshikimate + NADPH
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
L-quinate + NAD+
3-dehydroquinate + NADH + H+
L-quinate + NADP+
3-dehydroquinate + NADPH + H+
quinate + NAD(P)+
3-dehydroquinate + NAD(P)H + H+
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quinate + NAD+
3-dehydroquinate + NADH + H+
quinate + NADP+
3-dehydroquinate + NADPH + H+
shikimate + NAD(P)+
3-dehydroshikimate + NAD(P)H + H+
shikimate + NAD+
3-dehydroshikimate + NADH + H+
shikimate + NADP+
3-dehydroshikimate + NADPH
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
additional information
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3-dehydroquinate
3-dehydroshikimate + H2O
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r
3-dehydroquinate
3-dehydroshikimate + H2O
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DQD reaction
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r
3-dehydroquinate
3-dehydroshikimate + H2O
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r
3-dehydroquinate + NADH + H+
quinate + NAD+
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r
3-dehydroquinate + NADH + H+
quinate + NAD+
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r
3-dehydroquinate + NADPH + H+
quinate + NADP+
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r
3-dehydroquinate + NADPH + H+
quinate + NADP+
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r
3-dehydroshikimate + NAD(P)H + H+
shikimate + NAD(P)+
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r
3-dehydroshikimate + NAD(P)H + H+
shikimate + NAD(P)+
fourth enzyme involved in the shikimate pathway
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r
3-dehydroshikimate + NAD(P)H + H+
shikimate + NAD(P)+
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r
3-dehydroshikimate + NAD(P)H + H+
shikimate + NAD(P)+
fourth enzyme involved in the shikimate pathway
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r
3-dehydroshikimate + NADH + H+
shikimate + NAD+
less than 1% of the rate with 3-dehydroquinate
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r
3-dehydroshikimate + NADH + H+
shikimate + NAD+
less than 1% of the rate with 3-dehydroquinate
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r
3-dehydroshikimate + NADP+
gallate + NADPH + H+
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r
3-dehydroshikimate + NADP+
gallate + NADPH + H+
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r
3-dehydroshikimate + NADPH
?
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enzyme of shikimic acid biosynthesis
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r
3-dehydroshikimate + NADPH
?
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pathway of biosynthesis of aromatic amino acids
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3-dehydroshikimate + NADPH
shikimate + NADP+
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r
3-dehydroshikimate + NADPH
shikimate + NADP+
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r
3-dehydroshikimate + NADPH
shikimate + NADP+
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r
3-dehydroshikimate + NADPH
shikimate + NADP+
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NADH may substitute for NADPH
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r
3-dehydroshikimate + NADPH
shikimate + NADP+
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-
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r
3-dehydroshikimate + NADPH
shikimate + NADP+
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?
3-dehydroshikimate + NADPH
shikimate + NADP+
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?
3-dehydroshikimate + NADPH
shikimate + NADP+
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?
3-dehydroshikimate + NADPH
shikimate + NADP+
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r
3-dehydroshikimate + NADPH
shikimate + NADP+
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SDH reaction
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r
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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structure of the enzyme is a compact alpha/beta sandwich with two distinct domains, responsible for binding substrate and NADP cofactor, respectively
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3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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r
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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r
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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r
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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?
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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r
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
catalytic mechanism, residue Lys69 plays a catalytic role and is not involved in substrate binding
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r
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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?, r
3-dehydroshikimate + NADPH + H+
shikimate + NADP+
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r
L-quinate + NAD+
3-dehydroquinate + NADH + H+
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r
L-quinate + NAD+
3-dehydroquinate + NADH + H+
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r
L-quinate + NADP+
3-dehydroquinate + NADPH + H+
activity of T381 enzyme mutants, not of wild-type enzyme, see also EC 1.1.1.282
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r
L-quinate + NADP+
3-dehydroquinate + NADPH + H+
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r
L-quinate + NADP+
3-dehydroquinate + NADPH + H+
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activity by only mutant S275G/T318G, not the wild-type enzyme
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r
quinate + NAD+
3-dehydroquinate + NADH + H+
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r
quinate + NAD+
3-dehydroquinate + NADH + H+
in contrast to shikimate, quinate may form a hydrogen bond to the NAD+, and the hydroxyl group of a active-site threonine hydrogen bonds to quinate more effectively than shikimate resulting in a lower Michaelis constant and higher catalytic efficiency for quinate
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quinate + NAD+
3-dehydroquinate + NADH + H+
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r
quinate + NAD+
3-dehydroquinate + NADH + H+
the fourth enzyme in the shikimate pathway
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quinate + NAD+
3-dehydroquinate + NADH + H+
the fourth enzyme in the shikimate pathway
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r
quinate + NADP+
3-dehydroquinate + NADPH + H+
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reversible activity of YdiB, no activity with paralogue HI0607
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r
quinate + NADP+
3-dehydroquinate + NADPH + H+
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r
quinate + NADP+
3-dehydroquinate + NADPH + H+
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r
shikimate + NAD(P)+
3-dehydroshikimate + NAD(P)H + H+
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?
shikimate + NAD(P)+
3-dehydroshikimate + NAD(P)H + H+
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?
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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-
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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-
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?
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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-
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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the enzyme is also active with NAD+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NAD+
3-dehydroshikimate + NADH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH
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assay at 24°C, pH 9.0
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shikimate + NADP+
3-dehydroshikimate + NADPH
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SDH reaction
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
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?
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
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?
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
Bambusa sp.
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shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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?
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
-
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?
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
-
r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
-
r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
-
-
-
r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
-
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?
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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-
-
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?
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
shikimate + NADP+
3-dehydroshikimate + NADPH + H+
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r
1.1.1.25 shikimate dehydrogenase (NADP+)
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