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EC Tree
IUBMB Comments Levoglucosan is formed from the pyrolysis of carbohydrates such as starch and cellulose and is an important molecular marker for pollution from biomass burning. This enzyme is present only in bacteria, and has been characterized from Arthrobacter sp. I-552 and Pseudarthrobacter phenanthrenivorans. cf. EC 2.7.1.232, levoglucosan kinase.
The enzyme appears in viruses and cellular organisms
Reaction Schemes
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=
3-dehydrolevoglucosan
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Synonyms
1,6-anhydro-beta-D-glucose dehydrogenase,
Asphe3_10730 , LgdA, LgdH,
more
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1,6-anhydro-beta-D-glucose dehydrogenase
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Asphe3_10730
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LgdA
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LgdH
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levoglucosan + NAD+ = 3-dehydrolevoglucosan + NADH + H+
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1,6-anhydro-beta-D-glucopyranose:NAD+ 3-oxidoreductase
Levoglucosan is formed from the pyrolysis of carbohydrates such as starch and cellulose and is an important molecular marker for pollution from biomass burning. This enzyme is present only in bacteria, and has been characterized from Arthrobacter sp. I-552 and Pseudarthrobacter phenanthrenivorans. cf. EC 2.7.1.232, levoglucosan kinase.
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3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
sorbose + NAD+
? + NADH + H+
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?
xylose + NAD+
? + NADH + H+
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?
additional information
?
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3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
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r
3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
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r
3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
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r
3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
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r
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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?
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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r
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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r
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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r
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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r
additional information
?
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the reaction follows a sequential mechanism. Catalytic activity is specific for levoglucosan and NAD+. Poor substrates: ribose and glucose
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additional information
?
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the reaction follows a sequential mechanism. Catalytic activity is specific for levoglucosan and NAD+. Poor or no substrates: ribose and glucose, mannose, galactose, fructose, fucose, rhamnose, galactosan, sedoheptulosan
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additional information
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about 4% of the activity with levoglucosan with L-sorbose and 1,5-anhydro-D-glucitol
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additional information
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about 4% of the activity with levoglucosan with L-sorbose and 1,5-anhydro-D-glucitol
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additional information
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about 4% of the activity with levoglucosan with L-sorbose and 1,5-anhydro-D-glucitol
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3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
sorbose + NAD+
? + NADH + H+
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?
xylose + NAD+
? + NADH + H+
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?
additional information
?
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the reaction follows a sequential mechanism. Catalytic activity is specific for levoglucosan and NAD+. Poor substrates: ribose and glucose
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3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
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r
3-dehydrolevoglucosan + NADH + H+
levoglucosan + NAD+
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r
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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?
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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r
levoglucosan + NAD+
3-dehydrolevoglucosan + NADH + H+
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r
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NAD+
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4-chloromercuribenzoate
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1 mM, complete loss of activity
Cd2+
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1 mM, about 30% residual activity
Cu2+
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1 mM, about 30% residual activity
additional information
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not inhibitory at 1 mM: Mg2+, Ca2+, K+, Na+, iodoacetic acid, EDTA, o-phenanthroline, ferricyanide
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14
levoglucosan
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pH 9, 40°C
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333
levoglucosan
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pH 9, 40°C
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0.65
substrate 1,5-anhydro-D-glucitol, pH 8.5, 40°C
0.73
substrate L-sorbose, pH 8.5, 40°C
1.32
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substrate levoglucosan, pH 7.5, 30°C
17.8
substrate levosan, pH 8.5, 40°C
6
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substrate 3-dehydrolevoglucosan, pH 7.5, 30°C
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brenda
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brenda
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brenda
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UniProt
brenda
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UniProt
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metabolism
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in the metabolic pathway from levoglucosan to glucose, LgdA (LGDH) catalyzes 3-dehydrogenation of levoglucosan to produce 3-keto-levoglucosan, which undergoes beta-elimination of 3-keto-levoglucosan by LgdB1, followed by hydration to produce 3-keto-D-glucose by LgdB2. Next, LgdC reduces 3-keto-D-glucose to glucose
metabolism
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in the metabolic pathway from levoglucosan to glucose, LgdA (LGDH) catalyzes 3-dehydrogenation of levoglucosan to produce 3-keto-levoglucosan, which undergoes beta-elimination of 3-keto-levoglucosan by LgdB1, followed by hydration to produce 3-keto-D-glucose by LgdB2. Next, LgdC reduces 3-keto-D-glucose to glucose
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F0M433_PSEPM
Pseudarthrobacter phenanthrenivorans (strain DSM 18606 / JCM 16027 / LMG 23796 / Sphe3)
390
0
42118
TrEMBL
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oligomer
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x * 28000 plus x * 21000, SDS-PAGE
?
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x * 44000, SDS-PAGE
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x * 44000, SDS-PAGE
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tetramer
4 * 42000, SDS-PAGE, 4 * 44280, calculated from sequence
tetramer
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4 * 42000, SDS-PAGE, 4 * 44280, calculated from sequence
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structures of LgdH in the apo and complex forms with NADH, NADH plus levoglucosan, and NADH plus L-sorbose. LgdH has a typical fold of Gfo/Idh/MocA family proteins. The active site recognizes the levoglucosan molecule with six hydrogen bonds, and the C3 atom of levoglucosan is closely located to the C4 atom of NADH nicotinamide
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expression in Escherichia coli
expression in Escherichia coli
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expression in Escherichia coli
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Nakahara, K.; Kitamura, Y.; Yamagishi, Y.; Shoun, H.; Yasui, T.
Levoglucosan dehydrogenase involved in the assimilation of levoglucosan in Arthrobacter sp. I-552
Biosci. Biotechnol. Biochem.
58
2193-2196
1994
Arthrobacter sp. I-552
brenda
Sugiura, M.; Nakahara, M.; Yamada, C.; Arakawa, T.; Kitaoka, M.; Fushinobu, S.
Identification, functional characterization, and crystal structure determination of bacterial levoglucosan dehydrogenase
J. Biol. Chem.
293
17375-17386
2018
Pseudarthrobacter phenanthrenivorans (F0M433), Pseudarthrobacter phenanthrenivorans, Pseudarthrobacter phenanthrenivorans DSM 18606 (F0M433)
brenda
Kuritani, Y.; Sato, K.; Dohra, H.; Umemura, S.; Kitaoka, M.; Fushinobu, S.; Yoshida, N.
Conversion of levoglucosan into glucose by the coordination of four enzymes through oxidation, elimination, hydration, and reduction
Sci. Rep.
10
20066
2020
Bacillus smithii, Bacillus smithii S-2701M
brenda
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