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(R)-1-phenyl-1,2-ethanediol + O2
? + H2O2
-
-
-
?
(S)-1-phenyl-1,2-ethanediol + O2
? + H2O2
-
-
-
?
1-phenyl-1,2-ethanediol + O2
? + H2O2
-
-
-
?
D-mannitol + O2
?
-
-
-
?
D-mannitol + O2
? + H2O2
-
-
-
?
D-sorbitol + O2
?
-
-
-
?
D-sorbitol + O2
? + H2O2
-
-
-
?
glycerol + O2
? + H2O2
-
-
-
?
xylitol + O2
xylose + H2O2
-
-
-
?
(R)-1-phenyl-1,2-ethanediol + O2
?
-
-
-
-
?
(R)-1-phenyl-1,2-ethanediol + O2
hydroxy(phenyl)acetic acid + H2O2
-
-
product identification by NMR
-
?
(R)-1-phenyl-1,2-ethanediol + O2
mandelic acid + H2O2
-
the enzyme is highly enantioselective for the oxidation of (R)-1-phenyl-1,2-ethanediol
-
-
?
(S)-1-phenyl-1,2-ethanediol + O2
?
-
-
-
-
?
1,2,4-butanetriol + O2
?
-
-
-
-
?
1,2-butanediol + O2
?
-
-
-
-
?
1,2-hexanediol + O2
?
-
-
-
-
?
1,2-pentanediol + O2
2-hydroxypentanoic acid + H2O2
1,2-propanediol + O2
?
-
-
-
-
?
1,3,5-pentanetriol + O2
?
-
-
-
-
?
1,3-butanediol + O2
3-hydroxybutanal + H2O2
-
-
product identification by GC-MS
-
?
1,4-butanediol + O2
?
-
very poor substrate
-
-
?
1-phenyl-1,2-ethanediol + O2
?
-
the enzyme is highly enantioselective for the oxidation of 1-phenyl-1,2-ethanediol, 35% conversion to mandelic acid and two minor by-products (less than 5%) is observed after 65 h
-
-
?
2-amino-1-pentanol + O2
?
-
-
-
-
?
3-butene-1,2-diol + O2
?
-
-
-
-
?
3-butenol + O2
?
-
-
-
-
?
4-pentene-1,2-diol + O2
?
-
-
-
-
?
cis-2-butene-1,4-diol + O2
?
-
-
-
-
?
D-galactose + O2
?
-
very poor substrate
-
-
?
D-glyceraldehyde + O2
D-glycerate + H2O2
-
-
-
-
?
D-mannitol + O2
?
-
-
-
-
?
D-sorbitol + O2
?
-
-
-
-
?
glycerol + O2
?
-
-
-
-
?
glycerol + O2
D-glyceraldehyde + H2O2
-
-
-
-
?
glycerol + O2
glyceraldehyde + H2O2
-
-
-
-
?
L-threitol + O2
?
-
-
-
-
?
sorbitol + O2
?
-
-
-
-
?
xylitol + O2
D-xylose + H2O2
-
best substrate
-
-
?
xylitol + O2
xylose + H2O2
-
-
-
-
?
additional information
?
-
1,2-pentanediol + O2
2-hydroxypentanoic acid + H2O2
-
-
product identification by NMR
-
?
1,2-pentanediol + O2
2-hydroxypentanoic acid + H2O2
-
50% conversion after 22 h
-
-
?
L-arabinose + O2
?
-
-
-
-
?
L-arabinose + O2
?
-
very poor substrate
-
-
?
xylitol + O2
?
-
-
-
-
?
xylitol + O2
?
-
best substrate
-
-
?
additional information
?
-
-
AldO catalyzes the C1 oxidation of several polyols
-
-
?
additional information
?
-
-
substrate specificity, besides alditols, 1,2-diols are reasonable substrates indicating that two adjacent hydroxy groups at C-1 and C-2 seem to be a minimal requirement for a compound in order to be effectively oxidized by AldO, overview
-
-
?
additional information
?
-
-
the enzyme is able to perform oxidations of alcohols into aldehydes/ketones (single oxidation) and oxidations of alcohols into acids (double oxidation)
-
-
?
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101
(R)-1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
86
(S)-1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
83
1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
36
D-mannitol
pH 7.5, 25°C, recombinant enzyme
1.4
D-sorbitol
pH 7.5, 25°C, recombinant enzyme
350
glycerol
pH 7.5, 25°C, recombinant enzyme
10 - 101
(R)-1-phenyl-1,2-ethanediol
86
(S)-1-phenyl-1,2-ethanediol
83
1-phenyl-1,2-ethanediol
additional information
additional information
-
0.29 - 0.35
xylitol
recombinant oxidase-peroxidase fusion mutant enzyme, pH 7.5, temperature not specified in the publication
0.32
xylitol
pH 7.5, 25°C, recombinant enzyme
10
(R)-1-phenyl-1,2-ethanediol
-
pH 7.5, 30°C
101
(R)-1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
86
(S)-1-phenyl-1,2-ethanediol
-
pH 7.5, 30°C
86
(S)-1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
170
1,2,4-butanetriol
-
pH 7.5, 30°C
170
1,2,4-butanetriol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
150
1,2-Butanediol
-
pH 7.5, 30°C
150
1,2-Butanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
97
1,2-hexanediol
-
pH 7.5, 30°C
97
1,2-hexanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
52
1,2-pentanediol
-
pH 7.5, 30°C
52
1,2-pentanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
83
1-phenyl-1,2-ethanediol
-
pH 7.5, 30°C
83
1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
35
2-amino-1-pentanol
-
pH 7.5, 30°C
35
2-amino-1-pentanol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
250
3-butene-1,2-diol
-
pH 7.5, 30°C
250
3-butene-1,2-diol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
480
3-butenol
-
pH 7.5, 30°C
480
3-butenol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
42
4-pentene-1,2-diol
-
pH 7.5, 30°C
42
4-pentene-1,2-diol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
36
D-mannitol
-
pH 7.5, 30°C
36
D-mannitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
1.4
D-sorbitol
-
pH 7.5, 30°C
1.4
D-sorbitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
350
glycerol
-
pH 7.5, 30°C
350
glycerol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
430
L-arabinose
-
pH 7.5, 30°C
430
L-arabinose
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
25
L-Threitol
-
pH 7.5, 30°C
25
L-Threitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.32
xylitol
-
pH 7.5, 30°C
0.32
xylitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
additional information
additional information
steady-state kinetic analysis, overview
-
additional information
additional information
-
substrate specificity and steady state kinetics, overview
-
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0.74
(R)-1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
0.008
(S)-1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
0.36
1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
9.2
D-mannitol
pH 7.5, 25°C, recombinant enzyme
17
D-sorbitol
pH 7.5, 25°C, recombinant enzyme
1.6
glycerol
pH 7.5, 25°C, recombinant enzyme
0.74
(R)-1-phenyl-1,2-ethanediol
0.008
(S)-1-phenyl-1,2-ethanediol
0.36
1-phenyl-1,2-ethanediol
9.1 - 12.2
xylitol
recombinant oxidase-peroxidase fusion mutant enzyme, pH 7.5, temperature not specified in the publication
13
xylitol
pH 7.5, 25°C, recombinant enzyme
0.74
(R)-1-phenyl-1,2-ethanediol
-
pH 7.5, 30°C
0.74
(R)-1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.008
(S)-1-phenyl-1,2-ethanediol
-
pH 7.5, 30°C
0.008
(S)-1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
4.4
1,2,4-butanetriol
-
pH 7.5, 30°C
4.4
1,2,4-butanetriol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.29
1,2-Butanediol
-
pH 7.5, 30°C
0.29
1,2-Butanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
2
1,2-hexanediol
-
pH 7.5, 30°C
2
1,2-hexanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.85
1,2-pentanediol
-
pH 7.5, 30°C
0.85
1,2-pentanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.36
1-phenyl-1,2-ethanediol
-
pH 7.5, 30°C
0.36
1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.017
2-amino-1-pentanol
-
pH 7.5, 30°C
0.017
2-amino-1-pentanol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.34
3-butene-1,2-diol
-
pH 7.5, 30°C
0.34
3-butene-1,2-diol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.1
3-butenol
-
pH 7.5, 30°C
0.1
3-butenol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.35
4-pentene-1,2-diol
-
pH 7.5, 30°C
0.35
4-pentene-1,2-diol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
9.2
D-mannitol
-
pH 7.5, 30°C
9.2
D-mannitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
17
D-sorbitol
-
pH 7.5, 30°C
17
D-sorbitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
1.6
glycerol
-
pH 7.5, 30°C
1.6
glycerol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
1.7
L-arabinose
-
pH 7.5, 30°C
1.7
L-arabinose
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
6.3
L-Threitol
-
pH 7.5, 30°C
6.3
L-Threitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
13
xylitol
-
pH 7.5, 30°C
13
xylitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
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0.0073
(R)-1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
0.0001
(S)-1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
0.0043
1-phenyl-1,2-ethanediol
pH 7.5, 25°C, recombinant enzyme
0.26
D-mannitol
pH 7.5, 25°C, recombinant enzyme
12
D-sorbitol
pH 7.5, 25°C, recombinant enzyme
0.0046
glycerol
pH 7.5, 25°C, recombinant enzyme
41
xylitol
pH 7.5, 25°C, recombinant enzyme
0.0073
(R)-1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0001
(S)-1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.026
1,2,4-butanetriol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0019
1,2-Butanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.021
1,2-hexanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.016
1,2-pentanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0003
1,2-propanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0078
1,3,5-pentanetriol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0043
1-phenyl-1,2-ethanediol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0006
2-amino-1-pentanol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0014
3-butene-1,2-diol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0002
3-butenol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0083
4-pentene-1,2-diol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0003
D-galactose
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.26
D-mannitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
12
D-sorbitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.0046
glycerol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.004
L-arabinose
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
0.25
L-Threitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
41
xylitol
-
in 50 mM sodium phosphate buffer, at pH 7.5 and 30°C
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synthesis
-
AldO is an enantioselective biocatalyst for the kinetic resolution of racemic 1,2-diols
synthesis
-
utilization of recombinant enzyme expressed in the periplasm or on the cell surface of Escherichia coli as biocatalyst in a non-laborious and non-costly whole-cell application for reacting on towards different polyols such as xylitol and sorbitol
synthesis
-
biosynthetic production of glycolate from glycerol using a variant of alditol oxidase, 2-hydroxyglutarate-pyruvate transhydrogenase from Saccharomyces cerevisiae, alpha-ketoisovalerate decarboxylase from Lactococcus lactis, and aldehyde dehydrogenase from Escherichia coli in an artificial operon expressed in Escherichia coli. To redirect glycerol flux toward glycolate synthesis, key genes of the native glycerol assimilation pathways are deleted and a second plasmid expressing Dld3 to reduce the accumulation of the intermediate D-glycerate is introduced. The final engineered strain produces 0.64 g/l glycolate in shake flasks, which is increased to 4.74 g/l in fed-batch fermentation
synthesis
-
one-pot biocatalytic system converting a range of triacylglycerols/natural oils into alpha-olefins. The system consists of CRL from Candida rugosa (for triacylglycerol hydrolysis to provide free fatty acids and glycerol), AldO (for in situ H2O2 generation upon glycerol oxidation), and OleTJE (for free fatty acid decarboxylation using H2O2 as cofactor) and is independent of exogenous addition of H2O2. The reaction system achieves a 68.5% total alkene yield from 500 microM coconut oil. About 0.5 g/l of alpha-olefins are produced from coconut oil (1500 microM) upon some reaction optimization
synthesis
-
production of ethylene glycol from glycerol by an artificial enzymatic cascade comprised of alditol oxidase, catalase, glyoxylate/hydroxypyruvate reductase, pyruvate decarboxylase and lactaldehyde:propanediol oxidoreductase. The NADH generated during the dehydrogenation of the glycerol oxidation product D-glycerate can be used as the reductant to support the ethylene glycol production. Using this in vitro synthetic system with self-sufficient NADH recycling, 7.64 mM ethylene glycol is produced from 10 mM glycerol in 10 h, with a yield of 0.515 g/g
synthesis
-
synthesis of rare ketoses from glycerol and D-/L-glyceraldehyde in a one-pot multienzyme fashion in which the only carbon source is glycerol. Glycerol is phosphorylated and then oxidized at C2 to afford dihydroxyacetone phosphate. The primary alcohol of glycerol is also oxidized to give the acceptor molecule glycerol aldehyde in situ (D- or L-isomer can be formed stereospecifically with either alditol oxidase or horse liver alcohol dehydrogenase). Different dihydroxyacetone phosphate-dependent aldolases are used to generate the aldol adducts (rare ketohexose phosphates) with various stereoconfigurations and diastereomeric ratios
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Van Hellemond, E.; Vermote, L.; Koolen, W.; Sonke, T.; Zandvoort, E.; Heuts, D.; Janssen, D.; Fraaije, M.
Exploring the biocatalytic scope of alditol oxidase from Streptomyces coelicolor
Adv. Synth. Catal.
351
1523-1530
2009
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
-
brenda
van Bloois, E.; Winter, R.T.; Janssen, D.B.; Fraaije, M.W.
Export of functional Streptomyces coelicolor alditol oxidase to the periplasm or cell surface of Escherichia coli and its application in whole-cell biocatalysis
Appl. Microbiol. Biotechnol.
83
679-687
2009
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
brenda
Forneris, F.; Heuts, D.; Delvecchio, M.; Rovida, S.; Fraaije, M.; Mattevi, A.
Structural analysis of the catalytic mechanism and stereoselectivity in Streptomyces coelicolor alditol oxidase
Biochemistry
47
978-985
2008
Streptomyces coelicolor (Q9ZBU1), Streptomyces coelicolor, Streptomyces coelicolor A3(2) (Q9ZBU1), Streptomyces coelicolor A3(2)
brenda
Winter, R.T.; Heuts, D.P.; Rijpkema, E.M.; van Bloois, E.; Wijma, H.J.; Fraaije, M.W.
Hot or not? Discovery and characterization of a thermostable alditol oxidase from Acidothermus cellulolyticus 11B
Appl. Microbiol. Biotechnol.
95
389-403
2012
Acidothermus cellulolyticus (A0LST6), Acidothermus cellulolyticus 11B (A0LST6), Acidothermus cellulolyticus 11B, Streptomyces coelicolor (Q9ZBU1), Streptomyces coelicolor A3(2) (Q9ZBU1), Streptomyces coelicolor A3(2)
brenda
Winter, R.T.; van den Berg, T.E.; Colpa, D.I.; van Bloois, E.; Fraaije, M.W.
Functionalization of oxidases with peroxidase activity creates oxiperoxidases: a new breed of hybrid enzyme capable of cascade chemistry
ChemBioChem
13
252-258
2012
Streptomyces coelicolor (Q9ZBU1), Streptomyces coelicolor A3(2) (Q9ZBU1), Streptomyces coelicolor A3(2)
brenda
Matthews, S.; Tee, K.L.; Rattray, N.J.; McLean, K.J.; Leys, D.; Parker, D.A.; Blankley, R.T.; Munro, A.W.
Production of alkenes and novel secondary products by P450 OleTJE using novel H2O2-generating fusion protein systems
FEBS Lett.
591
737-750
2017
Streptomyces coelicolor
brenda
Zhan, T.; Chen, Q.; Zhang, C.; Bi, C.; Zhang, X.
Constructing a novel biosynthetic pathway for the production of glycolate from glycerol in Escherichia coli
ACS Synth. Biol.
9
2600-2609
2020
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
brenda
Chen, Z.; Li, Z.; Li, F.; Wang, N.; Gao, X.D.
Characterization of alditol oxidase from Streptomyces coelicolor and its application in the production of rare sugars
Bioorg. Med. Chem.
28
115464
2020
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
brenda
Jiang, Y.; Li, Z.; Zheng, S.; Xu, H.; Zhou, Y.; Gao, Z.; Meng, C.; Li, S.
Establishing an enzyme cascade for one-pot production of alpha-olefins from low-cost triglycerides and oils without exogenous H2O2 addition
Biotechnol. Biofuels
13
52
2020
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
brenda
Li, K.; Sun, W.; Meng, W.; Yan, J.; Zhang, Y.; Guo, S.; Lue, C.; Ma, C.; Gao, C.
Production of ethylene glycol from glycerol using an in vitro enzymatic cascade
Catalysts
11
214
2021
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
-
brenda
Li, Z.; Li, F.; Cai, L.; Chen, Z.; Qin, L.; Gao, X.D.
One-pot multienzyme synthesis of rare ketoses from glycerol
J. Agric. Food Chem.
68
1347-1353
2020
Streptomyces coelicolor, Streptomyces coelicolor A3(2)
brenda