Ligand 1-propanol

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Basic Ligand Information

Molecular Structure
Picture of 1-propanol (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C3H8O
1-propanol
MLJYKRYCCUGBBV-YTWAJWBKSA-N
Synonyms:
n-Propanol, n-Propyl alcohol, propan-1-ol, Propane-1-ol, Propanol, Propyl alcohol


Show all pahtways known for Show all BRENDA pathways known for 1-propanol

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-propanol + NAD+ = propanal + NADH + H+
show the reaction diagram
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1-propanol + NAD(P)+ = propionaldehyde + NAD(P)H + H+
show the reaction diagram
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n-propanol + O2 = n-propanal + H2O2
show the reaction diagram
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n-propanol + O2 = propionaldehyde + H2O2
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxopentanedioic acid 5-propyl ester + H2O = 2-oxoglutarate + propanol
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (106 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
n-propanol + NAD+ = n-propanal + NADH
show the reaction diagram
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n-propanol + NAD+ + H2O = n-propanal + NADH
show the reaction diagram
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propanol + NADP+ = propionaldehyde + NADPH
show the reaction diagram
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1-propanol + NAD+ = propionaldehyde + NADH
show the reaction diagram
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1-propanol + NAD+ = propanal + NADH + H+
show the reaction diagram
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1-propanol + NAD+ = n-propanal + NADH
show the reaction diagram
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1-propanol + NAD+ = propanal + NADH + H+
show the reaction diagram
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n-propanol + NAD+ = n-propanal + NADH
show the reaction diagram
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propanol + NAD+ = propionaldehyde + NADH
show the reaction diagram
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propan-1-ol + NADP+ = propanal + NADPH + H+
show the reaction diagram
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1-propanol + NAD+ = propanal + NADH
show the reaction diagram
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propanol + 2 cytochrome c = propanal + 2 reduced cytochrome c
show the reaction diagram
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1-propanol + ferricytochrome c = propanal + ferrocytochrome c + H+
show the reaction diagram
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propanol + N,N,N',N'-tetramethyl-4-phenylenediamine = propionaldehyde + reduced N,N,N',N'-tetramethyl-4-phenylenediamine
show the reaction diagram
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1-propanol + acceptor = propanal + reduced acceptor
show the reaction diagram
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1-propanol + O2 = n-propanal + H2O2
show the reaction diagram
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1-propanol + O2 = propanal + H2O2
show the reaction diagram
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n-propanol + O2 = propionaldehyde + H2O2
show the reaction diagram
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1-propanol + a quinone = propanal + a quinol
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1-propanol + acceptor = n-propanal + reduced acceptor
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1-propanol + 2,6-dichloro-phenolindophenol = propanal + reduced 2,6-dichloro-phenolindophenol
show the reaction diagram
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propanol + O2 = ?
show the reaction diagram
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n-propanol + NAD+ + H2O = ? + NADH
show the reaction diagram
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1-propanol + p-nitroso-N,N-dimethylaniline = n-propanal + reduced p-nitroso-N,N-dimethylaniline
show the reaction diagram
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O-acetyl-L-homoserine + n-propanol = O-propyl-homoserine + acetic acid
show the reaction diagram
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3'-phosphoadenylylsulfate + 1-propanol = adenosine 3',5'-bisphosphate + 1-propyl sulfate
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oleate + 1-propanol = 1-propyl oleate + H2O
show the reaction diagram
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adenosine 5'-triphosphate + propanol = adenosine 5'-monophosphate-O-propyl ester + H2O + diphosphate
show the reaction diagram
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phosphatidylcholine + propanol = phosphatidylpropanol + choline
show the reaction diagram
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n-propanol + phenyl alpha-D-galactoside = ?
show the reaction diagram
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4-O-beta-D-mannopyranosyl-D-mannopyranose + 1-propanol = ?
show the reaction diagram
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N-acetyllactosamine + propanol = proyl beta-N-acetyllactosaminide + H2O
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di-N-acetylchitobiose + 1-propanol = ?
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dextran + 1-propanol = 1-propyl alpha-isomaltoside + H2O
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beta-D-Gal-(1-3)-alpha-D-GalNAc-(1-O)-p-nitrophenyl + 1-propanol = beta-D-Gal-(1-3)-alpha-D-GalNAc-(1-O)-propyl + p-nitrophenol
show the reaction diagram
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1-propanol + N-acetyl phenylalanine ethyl ester = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (90 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
propionaldehyde + NADPH = propanol + NADP+
show the reaction diagram
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propionaldehyde + NADH + H+ = propan-1-ol + NAD+
show the reaction diagram
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propanal + NAD(P)H + H+ = propanol + NAD(P)+
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propionaldehyde + NADPH = propanol + NADP+
show the reaction diagram
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propionaldehyde + NADH = 1-propanol + NAD+
show the reaction diagram
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propionaldehyde + reduced phenazine methosulfate = 1-propanol + phenazine methosulfate
show the reaction diagram
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propanal + ferrocyanide = 1-propanol + ferricyanide
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propanone + reduced coenzyme F420 = propanol + oxidized coenzyme F420
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propane + NADH + H+ + O2 = propan-1-ol + NAD+ + H2O
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propane + NAD(P)H + O2 = 1-propanol + 2-propanol + NAD(P)+ + H2O
show the reaction diagram
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N-propyl acetate + H2O = n-propanol + acetate
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propyl acetate + H2O = propanol + acetate
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propyl acetate + H2O = propanol + acetate
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n-propyl myristate + H2O = n-propanol + myristic acid
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propylthiocholine + H2O = thiocholine + propanol
show the reaction diagram
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dipropyl phthalate + H2O = 1,3-isobenzofurandione + propanol
show the reaction diagram
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pimeloyl-[acyl-carrier protein] propyl ester + H2O = pimeloyl-[acyl-carrier protein] + propanol
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n-Propyl-phosphate + H2O = n-Propanol + phosphate
show the reaction diagram
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propan-1-ol 2-phosphate + H2O = 1-propanol + phosphate
show the reaction diagram
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n-propyl alpha-D-galactoside + H2O = n-propanol + D-galactose
show the reaction diagram
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propyl alpha-L-fucopyranoside + H2O = propanol + alpha-L-fucopyranose
show the reaction diagram
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ethyl 2-(4-ethylphenoxy)propionate + butanol = butyl 2-(4-ethylphenoxy)propanoate + propanol
show the reaction diagram
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propyl glutarate + hydoxylamine = glutaramate + propanol
show the reaction diagram
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2-oxopentanedioic acid 5-propyl ester + H2O = 2-oxoglutarate + propanol
show the reaction diagram
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3-hydroxypropylflavin + H2O = propanol + lumichrome
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
10% v/v, 2.1fold activation
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increases maximal reaction rate
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slightly stimulating
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activates
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85%, activation
-
maximal activation, at 2.5 mM, inhibition above 25 mM
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activates at a concentration of 3.6-7.3% v/v, at higher concentration it inhibits the propyl gallate synthesis reaction causing disruption of essential membrane functions and denaturation of enzyme
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stimulates phospholipase A1 activity and inhibits lysophospholipase 1 activity
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slight activation
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20 mM, activates, highest rate of consumption of p-nitrophenyl beta-D-glucopyranoside in the presence of 0.6 M 1-propanol
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maximal stimulation at 7.5%
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the liberation of aglycone from aryl beta-D-glucosides is stimulated by alcohols in a manner suggesting specific interaction between alcohol and enzyme
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alcohol modifies the protein microenvironment, leading to a more flexible enzyme structure, which is probably responsible for the enhanced enzymatic activity
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subtilisin precipitated and rinsed with propanol yields higher transesterfication activity. About 10000times increase in initial rates in 1-butyl-3-methylimidazolium hexafluorophosphate over what is obtained with pH tuned lyophilized powders
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activation e.g. between 1.5-5%, v/v, depending on substrate
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activating at concentrations below 1.5 M
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stimulation by aliphatic alcohols in a decreasing order of effectiveness: ethylene glycol > 2-propanol > ethanol > glycerol > methanol > 1-propanol
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isoform AC6 shows about 31% stimulation of activity with 100 mM 1-propanol, isoform AC7 shows about 50% stimulation of activity with 100 mM 1-propanol, isoform AC9 shows about 44% stimulation of activity with 100 mM 1-propanol
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1.6fold increase of activity when added to the enzyme test system at a concentration of 6%
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Inhibitor in Enzyme-catalyzed Reactions (55 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
5% v/v: 25-60% loss of activity, depending on substrate, enzyme regains activity after removal of alcohol
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substrate inhibition
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80% inhibition at 30% concentration as co-solvent
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IC50 of 2.5 vol%
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substrate n-butanol
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23% inhibition at 50 mM
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concentrations above 0.025 M
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about 99% inhibition at 1% (v/v)
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at concentrations greater than 5times Km
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strong inhibition at 10% v/v
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reversible noncompetitive
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30% inhibition at 10%, 50% at 20%
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inhibition above 50 mM
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transglycosylation, inactivation
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Ki: 11 mM
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reduces the residual activity to about 80 % when tested at concentrations of 10 and 30%. Activity is not affected using 50%
-
inhibition of esterolytic activity
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competitive to ethanoamine
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about 22% residual activity at 5% (v/v)
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inhibitory at concentrations above 1.5 M
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3D Structure of Enzyme-Ligand-Complex (PDB) (381 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (20 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
12.8
-
pH 7.5, 37°C, recombinant enzyme
17.5
-
pH 7.5, 30°C
0.183
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pH 7.5, 37°C

KM Value (72 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
13
-
pH 7.5, 37°C, recombinant enzyme
324
-
-
46
-
pH and temperature not specified in the publication
0.0275
-
37°C, pH 9.0
4
-
pH 8.5, 30°C
10.7
-
pH 9.0, 30°C, assayed with N,N,N',N'-tetramethyl-4-phenylenediamine
2
-
strain DSM 4025
6.6
-
-
0.0039
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pH 7.0, 45°C
50
-
-
0.0032
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+ p-nitroso-N,N-dimethylaniline
2.4
-
pH 7.5, 30°C
530
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pH 7.2, 37°C, cosubstrate oleate

Ki Value (10 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
33.6
-
pH 7.5, 25°C, recombinant enzyme
4
-
pH 7.0, 45°C
21
-
-
70
-
substrate n-butanol
250
-
-
11
-
-

References & Links

Links to other databases for 1-propanol

ChEBI
PubChem
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PubChem