Ligand D-fructofuranose

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Basic Ligand Information

Molecular Structure
Picture of D-fructofuranose (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H12O6
D-fructofuranose
RFSUNEUAIZKAJO-VRPWFDPXSA-N
Synonyms:
arabino-hexulose, D-(-)-fructose, D-(-)-Levulose, D-fructose, fructose, Fruit sugar, levulose

Show all pahtways known for Show all pathways known for D-fructofuranose

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
fructose + NADPH = sorbitol + NADP+
show the reaction diagram
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D-fructose + NADP+ = 5-dehydro-D-fructose + NADPH
show the reaction diagram
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D-fructose + NADPH = D-mannitol + NADP+
show the reaction diagram
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D-fructose + NADH + H+ = D-mannitol + NAD+
show the reaction diagram
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D-fructose + ferricenium ion = ? + ferrocene
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 1-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 6-phosphate
show the reaction diagram
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D-fructose = D-psicose
show the reaction diagram
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D-fructose = D-mannose
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (63 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
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sorbitol + NAD+ = D-fructose + NADH
show the reaction diagram
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sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
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-
D-mannitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
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D-mannitol + ferricytochrome c = D-fructose + ferrocytochrome c
show the reaction diagram
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D-glucitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
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D-fructose 1-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
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inulin + H2O = D-fructose + ?
show the reaction diagram
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sucrose + H2O = alpha-D-glucose + D-fructose
show the reaction diagram
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lactulose + H2O = D-fructose + D-galactose
show the reaction diagram
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4-O-beta-D-galactopyranosyl-D-fructoside + H2O = beta-D-galactose + D-fructose
show the reaction diagram
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levan + H2O = fructose + beta-1,2-oligofructans
show the reaction diagram
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fructans + H2O = D-fructose
show the reaction diagram
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sucrose 6-phosphate + H2O = glucose 6-phosphate + fructose
show the reaction diagram
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D-psicose = D-fructose
show the reaction diagram
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-
D-Glucose = D-Fructose
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (137 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-fructose + NADPH + H+ = ? + NADP+
show the reaction diagram
-
D-fructose + NADH + H+ = D-mannitol + NAD+
show the reaction diagram
-
D-fructose + NADH + H+ = D-sorbitol + NAD+
show the reaction diagram
-
fructose + NADPH = sorbitol + NADP+
show the reaction diagram
-
D-fructose + NADP+ = 5-dehydro-D-fructose + NADPH
show the reaction diagram
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D-fructose + NADPH = ? + NADP+
show the reaction diagram
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D-fructose + NAD(P)H + H+ = D-arabino-hexitol + NAD(P)+
show the reaction diagram
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D-fructose + NADPH = D-mannitol + NADP+
show the reaction diagram
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D-fructose + NADPH = 5-dehydro-D-fructose + NADP+
show the reaction diagram
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D-fructose + O2 = ?
show the reaction diagram
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D-fructose + 2,6-dichloroindophenol = ? + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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fructose + 2,6-dichlorophenolindophenol = ?
show the reaction diagram
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D-fructose + acceptor = 2-keto-D-gulonate + reduced acceptor
show the reaction diagram
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D-fructose + oxidized 2,6-dichlorophenolindophenol = 5-dehydro-D-fructose + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
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D-fructose + O2 = ?
show the reaction diagram
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acetyl-CoA + D-fructose = CoA + 6-O-acetyl-D-fructose
show the reaction diagram
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soluble starch + D-fructose = ?
show the reaction diagram
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UDP-alpha-D-glucose + D-fructose = ?
show the reaction diagram
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D-fructose + alpha-D-mannose 1-phosphate = ? + phosphate
show the reaction diagram
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D-fructose + alpha-D-mannose 1-phosphate = ? + phosphate
show the reaction diagram
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ATP + fructose = ADP + fructose 1-phosphate
show the reaction diagram
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phosphohistidinoprotein + D-fructose = histidine-containing protein + ?
show the reaction diagram
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glycerol 3-phosphate + D-fructose = ?
show the reaction diagram
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ADP + D-fructose = AMP + D-fructose 6-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 5-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 5-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + O3-phosphono-D-fructose
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 6-phosphate
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 1-phosphate
show the reaction diagram
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D-fructose + acetyl phosphate = D-fructose 1-phosphate + D-fructose 6-phosphate + acetate
show the reaction diagram
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phosphoramidate + fructose = fructose 1-phosphate + NH3
show the reaction diagram
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ATP + D-fructose = ADP + D-fructose 6-phosphate
show the reaction diagram
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phosphoenolpyruvate + fructose = pyruvate + fructose 1-phosphate
show the reaction diagram
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ferulic acid + D-fructose = ?
show the reaction diagram
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phosphatidylcholine + D-fructose = phosphatidylfructose + choline
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lactose + fructose = ?
show the reaction diagram
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4-O-beta-D-mannopyranosyl-D-mannopyranose + D-fructose = ?
show the reaction diagram
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fructose + H2O = ?
show the reaction diagram
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fructose + H2O = ?
show the reaction diagram
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D-fructose = D-glucose + D-mannose
show the reaction diagram
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D-fructose = D-tagatose
show the reaction diagram
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D-fructose = D-psicose
show the reaction diagram
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D-fructose = D-mannose
show the reaction diagram
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D-fructose = D-glucose + D-mannose
show the reaction diagram
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D-fructose = D-mannose
show the reaction diagram
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D-fructose = D-mannose
show the reaction diagram
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D-Fructose + alpha-D-glucose 1-phosphate = D-Fructose 6-phosphate + D-glucose
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (376 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-mannitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
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D-sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
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-
sorbitol + NAD+ = D-fructose + NADH + H+
show the reaction diagram
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-
D-glucosone + NADPH + H+ = D-fructose + NADP+
show the reaction diagram
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-
5-dehydro-D-fructose + NADPH = D-fructose + NADP+
show the reaction diagram
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-
D-mannitol + acceptor = D-fructose + reduced acceptor
show the reaction diagram
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D-xylulose 5-phosphate + D-erythrose = glyceraldehyde 3-phosphate + D-fructose
show the reaction diagram
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sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
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D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
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-
D-fructose 1-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
-
-
D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
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D-fructose 6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
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saccharose + H2O = D-glucose + D-fructose
show the reaction diagram
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sucrose + H2O = D-glucose + D-fructose
show the reaction diagram
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lactulose + H2O = D-galactose + D-fructose
show the reaction diagram
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4-O-beta-D-galactopyranosyl-D-fructoside + H2O = beta-D-galactose + D-fructose
show the reaction diagram
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sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
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sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
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sucrose + H2O = D-glucose + D-fructose
show the reaction diagram
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D-fructose-6-phosphate + H2O = D-fructose + phosphate
show the reaction diagram
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sucrose + H2O = D-fructose + D-glucose
show the reaction diagram
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2 D-glyceraldehyde = D-fructose
show the reaction diagram
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levan = di-D-fructose-2,6':2',6 dianhydride + fructose + limited levan
show the reaction diagram
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mannose = D-glucose + D-fructose
show the reaction diagram
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D-tagatose = D-fructose
show the reaction diagram
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D-psicose = D-fructose
show the reaction diagram
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D-glucose = D-fructose + D-mannose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
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D-Mannose = D-Fructose
show the reaction diagram
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Fructose 1-phosphate + D-glucose = D-glucose 6-phosphate + fructose
show the reaction diagram
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sucrose = palatinose + trehalulose + D-glucose + D-fructose
show the reaction diagram
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sucrose = D-glucose + D-fructose + [alpha-D-glucopyranosyl-(1,1)-D-fructofuranose]
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
17% activation at 2 mM
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minor stimulatory effect
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slight activation
increase of activity
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favores CGTase synthesis
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stimulates, stimulation pattern of MtrA is similar to that of MtrB
25 mM, 1.3fold stimulation, enzyme from maize endosperm
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the activity of 5'-nucleotidase increases with increasing D-fructose concentrations (5-30 mM) in diabetic patients
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slightly stimulating
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threefold activation
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58% activation at 3 mM
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Inhibitor in Enzyme-catalyzed Reactions (176 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
PtNADP-ME1
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substrate inhibition, Ki: 1.356 mM
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incubation of Aspergillus niger glucose oxidase with 100 mM fructose for 8 days results in 88% loss in activity
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D-fructose at different concentrations, PPO activities are measured at 25C and pH 7.0 to determine inhibitor effects of sugars on enzymatic activities. PPO activities from both cultivars show a decreasing pattern as sugar concentration in the assay medium increases
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25-30% inhibition at 20 mM
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competitive
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0.0015 mM almost totally inhibits uptake of D-mannose
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a 40fold excess of unlabeled D-fructose reduces maltose uptake to about 30-40% of the control rate
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0.2 M: 24% inhibition
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competitive to glucose
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inactivation of the glyoxalase system (glyoxalase I and II) in fructose fed mice
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0.95 M: 30% inhibition
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10 mM, 45% inhibition. Inhibitory effect is abolished by Ca2+
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5 mM, slight inhibition of starch hydrolysis
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reduced to 70% by the presence of 100 mM
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diminishes hdc gene expression
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10 mM, 19% inhibition
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2 mM ibuprofen and its major metabolites protect by up to 26%. Ibuprofen and the metabolites do not bind to fumarase
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formation of a Schiff base with the critical lysine residue of the enzyme is involved in inhibition of the enzyme by hexoses and pentoses
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Metals and Ions (3 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5 mM, 76.8% activity compared to activity without addition of MgCl2, 1.25 mM 4-nitrophenyl beta-D-xylopyranoside as substrate, pH 4.6, 42C; 5 mM, 86.6% activity compared to activity without addition of MgCl2, 1.25 mM 4-nitrophenyl beta-D-xylopyranoside as substrate, pH 4.6, 40C
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3D Structure of Enzyme-Ligand-Complex (PDB) (46 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (79 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
224
-
pH 6.0, 25C
154
-
pH 7.5, 25C, positive cooperativity
920
-
25C, pH 7.5, Tris-HCl
200
-
-
3.9
-
30C, pH 6
2
-
pH 5.0, 30C, synthetic reaction
17.5
-
in 50 mM glycine-NaOH buffer (pH 9.0), at 40C

KM Value (271 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
96
-
pH 8.6, 25C
600
-
-
9.6
-
-
19.8
-
at pH 7.0 and 30C
162
-
-
390
-
in 50 mM Bis-Tris propane (pH 8.0), at 50C
199
-
-
1.5
-
30C, pH 6
0.2
-
pH 5.0, 30C, synthetic reaction
1
-
pH 6.7, 85C
50
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pH 8.0, 37C
51
-
in 50 mM glycine-NaOH buffer (pH 9.0), at 40C

Ki Value (29 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1356
-
-
27
-
-
0.23
-
inhibition with respect to glucose

IC50 Value (4 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
40
-
pH 7.5, 30C, phosphopfructokinase reaction
40
-
pH 7.5, 30Cphosphopfructokinase reaction

References & Links