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D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
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D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism, overview
-
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism, overview
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism, overview
-
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism, overview
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
catalyric reaction mechanism and substrate specificity, overview
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
DOIS catalyzes the multi-step and direct cyclization reaction of G-6-P consisting five crucial transformations, which include the initial NAD+-dependent dehydrogenation at C-4, the elimination of a phosphate from C-5 and C-6, the hydride comeback to C-4 to form a cyclic enol ether, and the finial aldol-type intramolecular condensation between C-6 and C-1
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction and stereochemical mechanisms, overview
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism of the multistep reaction, stereochemistry of the phosphate elimination reaction, proceeding through syn-elimination assisted by Glu 243, and the cyclization, an aldol condensation that proceeds via a boat conformation, overview
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
the reaction mechanism includes oxidation of C-4, beta-elimination of phosphate, reduction of C-4, ring opening, and intramolecular aldol cyclization. Completely conserved E243 of BtrC is catalytically involved in the phosphate elimination step
D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism, overview
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D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
catalyric reaction mechanism and substrate specificity, overview
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D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism, overview
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D-glucose 6-phosphate = 2-deoxy-L-scyllo-inosose + phosphate
reaction mechanism of the multistep reaction, stereochemistry of the phosphate elimination reaction, proceeding through syn-elimination assisted by Glu 243, and the cyclization, an aldol condensation that proceeds via a boat conformation, overview
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2-deoxy-D-glucose 6-phosphate
2,5-dideoxy-L-scyllo-inosose + phosphate
3-deoxy-D-glucose 6-phosphate
2,4-dideoxy-L-scyllo-inosose + phosphate
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
additional information
?
-
2-deoxy-D-glucose 6-phosphate
2,5-dideoxy-L-scyllo-inosose + phosphate
low activity
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-
?
2-deoxy-D-glucose 6-phosphate
2,5-dideoxy-L-scyllo-inosose + phosphate
low activity
-
-
?
3-deoxy-D-glucose 6-phosphate
2,4-dideoxy-L-scyllo-inosose + phosphate
low activity
-
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?
3-deoxy-D-glucose 6-phosphate
2,4-dideoxy-L-scyllo-inosose + phosphate
low activity
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
carbocycle formation
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, mechanism, overview
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, multistep process
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
multistep reaction
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
the enzyme converts ubiquitous D-glucose 6-phosphate into the specific carbocycle, 2-deoxy-scyllo-inosose with an aid of NAD+-NADH recycling
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
cyclization stereochemistry, overview
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, hydride abstraction and returning appeared to take place within the same glucose molecule
product identification by GC-MS analysis
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
pro-R stereospecific hydride transfer by NAD+-catalyzed 2-deoxy-scyllo-inosose synthase
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
carbocycle formation
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
multistep reaction
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, mechanism, overview
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, hydride abstraction and returning appeared to take place within the same glucose molecule
product identification by GC-MS analysis
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, multistep process
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
intramolecular carbocyclization, multistep process
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-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
intramolecular carbocyclization, multistep process
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
additional information
?
-
the hydroxy group at C-4 is essential for enzyme activity, while the hydroxy groups at C-2 and C-3 are significant for efficial transformation of natural glucose 6-phosphate, but not essential for the reaction catalysis at the active site of enzyme, no activity with 4-deoxy-glucose 6-phosphate, substrate specificity, overview
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?
additional information
?
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specific hydrogen-bond accepting and donating interactions between the hydroxy groups at C-2 and C-3 of the substrate and the enzyme are responsible for the recognition
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?
additional information
?
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substrate specificity of 2-deoxy-scyllo-inosose synthase towards deoxyglucose 6-phosphates and proposed mechanism
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?
additional information
?
-
the hydroxy group at C-4 is essential for enzyme activity, while the hydroxy groups at C-2 and C-3 are significant for efficial transformation of natural glucose 6-phosphate, but not essential for the reaction catalysis at the active site of enzyme, no activity with 4-deoxy-glucose 6-phosphate, substrate specificity, overview
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?
additional information
?
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substrate specificity of 2-deoxy-scyllo-inosose synthase towards deoxyglucose 6-phosphates and proposed mechanism
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?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
additional information
?
-
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
carbocycle formation
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, mechanism, overview
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-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, multistep process
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
multistep reaction
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
the enzyme converts ubiquitous D-glucose 6-phosphate into the specific carbocycle, 2-deoxy-scyllo-inosose with an aid of NAD+-NADH recycling
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
carbocycle formation
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
multistep reaction
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, mechanism, overview
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
intramolecular carbocyclization, multistep process
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
intramolecular carbocyclization, multistep process
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
intramolecular carbocyclization, multistep process
-
-
?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
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?
D-glucose 6-phosphate
2-deoxy-L-scyllo-inosose + phosphate
-
-
-
-
?
additional information
?
-
the hydroxy group at C-4 is essential for enzyme activity, while the hydroxy groups at C-2 and C-3 are significant for efficial transformation of natural glucose 6-phosphate, but not essential for the reaction catalysis at the active site of enzyme, no activity with 4-deoxy-glucose 6-phosphate, substrate specificity, overview
-
-
?
additional information
?
-
the hydroxy group at C-4 is essential for enzyme activity, while the hydroxy groups at C-2 and C-3 are significant for efficial transformation of natural glucose 6-phosphate, but not essential for the reaction catalysis at the active site of enzyme, no activity with 4-deoxy-glucose 6-phosphate, substrate specificity, overview
-
-
?
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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0.017 - 20
D-glucose 6-phosphate
additional information
additional information
-
0.017
D-glucose 6-phosphate
pH 7.7, 35°C, native enzyme
0.11
D-glucose 6-phosphate
pH 7.7, 37°C, recombinant mutant E243Q
0.21
D-glucose 6-phosphate
pH 7.7, 46°C
0.21
D-glucose 6-phosphate
pH 7.7, 46°C, recombinant enzyme
0.23
D-glucose 6-phosphate
pH 7.7, 35°C, recombinant wild-type enzyme, BtrC
0.23
D-glucose 6-phosphate
pH 7.7, 37°C, recombinant wild-type enzyme
0.42
D-glucose 6-phosphate
pH 7.7, 35°C, recombinant wild-type enzyme, BtrC + BtrC2
0.69
D-glucose 6-phosphate
-
pH not specified in the publication, 46°C
0.9
D-glucose 6-phosphate
pH 7.7, 46°C
20
D-glucose 6-phosphate
above, pH 7.7, 37°C, recombinant mutant K141Q
additional information
additional information
steady state and pre-steady state kinetic analysis, overview
-
additional information
additional information
-
steady state and pre-steady state kinetic analysis, overview
-
Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
0.007 - 1
D-glucose 6-phosphate
0.007
D-glucose 6-phosphate
below, pH 7.7, 37°C, recombinant mutant K141Q
0.017
D-glucose 6-phosphate
pH 7.7, 37°C, recombinant mutant E243Q
0.073
D-glucose 6-phosphate
pH 7.7, 35°C, native enzyme
0.073
D-glucose 6-phosphate
pH 7.7, 46°C
0.075
D-glucose 6-phosphate
-
pH not specified in the publication, 46°C
0.41
D-glucose 6-phosphate
pH 7.7, 37°C, recombinant wild-type enzyme
0.44
D-glucose 6-phosphate
pH 7.7, 35°C, recombinant wild-type enzyme, BtrC + BtrC2
1
D-glucose 6-phosphate
pH 7.7, 35°C, recombinant wild-type enzyme, BtrC
1
D-glucose 6-phosphate
pH 7.7, 46°C, recombinant enzyme
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Please wait a moment until the data is sorted. This message will disappear when the data is sorted.
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4.2.3.124 2-deoxy-scyllo-inosose synthase
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