Information on EC 1.1.1.133 - dTDP-4-dehydrorhamnose reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY
1.1.1.133
-
RECOMMENDED NAME
GeneOntology No.
dTDP-4-dehydrorhamnose reductase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
dTDP-beta-L-rhamnose + NADP+ = dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
show the reaction diagram
in the reverse direction, reduction on the 4-position of the hexose moiety takes place only while the substrate is bound to another enzyme which catalyzes epimerization at C-3 and C-5; the complex has been referred to as dTDP-L-rhamnose synthase
-
-
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
dTDP-L-rhamnose biosynthesis I
-
Metabolic pathways
-
Polyketide sugar unit biosynthesis
-
Streptomycin biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
dTDP-6-deoxy-beta-L-mannose:NADP+ 4-oxidoreductase
In the reverse direction, reduction on the 4-position of the hexose moiety takes place only while the substrate is bound to another enzyme that catalyses epimerization at C-3 and C-5; the complex has been referred to as dTDP-L-rhamnose synthase.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
4-ketoreductase
-
-
bifunctional UDP-4-keto-6-deoxy-D-glucose epimerase/reductase
E3VXL5
-
dTDP-4-dehydrorhamnose reductase
-
-
dTDP-4-keto-L-rhamnose reductase
-
-
-
-
dTDP-4-keto-rhamnose reductase
-
-
dTDP-4-ketorhamnose reductase
-
-
-
-
dTDP-6-deoxy-L-lyxo-4-hexulose reductase
-
-
dTDP-6-deoxy-L-lyxo-4-hexulose reductase
Aggregatibacter actinomycetemcomitans NCTC 9710
-
-
-
dTDP-6-deoxy-L-lyxo-4-hexulose reductase
-
-
dTDP-6-deoxy-L-lyxo-4-hexulose reductase
-
-
dTDP-6-deoxy-L-mannose dehydrogenase
-
-
-
-
dTDP-L-rhamnose synthetase
-
-
-
-
TDP-4-keto-rhamnose reductase
-
-
-
-
TDP-4-ketorhamnose reductase
-
-
-
-
thymidine diphosphate-4-dehydrorhamnose reductase
-
-
thymidine diphosphate-6-deoxy-L-talose
-
-
thymidine diphosphate-6-deoxy-L-talose
Aggregatibacter actinomycetemcomitans NCTC 9710
-
-
-
thymidine diphospho-4-ketorhamnose reductase
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
37250-64-9
-
ORGANISM
COMMENTARY
LITERATURE
SEQUENCE CODE
SEQUENCE DB
SOURCE
gene L780
E3VXL5
UniProt
Manually annotated by BRENDA team
bifunctional 3,5-epimerase/4-keto reductase
Swissprot
Manually annotated by BRENDA team
Escherichia coli K12
K12
-
-
Manually annotated by BRENDA team
Escherichia coli O45
O45
-
-
Manually annotated by BRENDA team
sedovar typhimurium
-
-
Manually annotated by BRENDA team
serovar typhimurium LT2
-
-
Manually annotated by BRENDA team
serovar typhimurium, LT2, gene rmlD
-
-
Manually annotated by BRENDA team
Streptomyces mutans
-
-
-
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
dTDP-4-dehydro-6-deoxy-D-glucose + NADH + H+
dTDP-beta-L-rhamnose + NAD+
show the reaction diagram
-
-
-
-
-
dTDP-4-dehydro-6-deoxy-D-glucose + NADH + H+
dTDP-beta-L-rhamnose + NAD+
show the reaction diagram
Q9LQ04
40% of the rate with NADPH
-
-
?
dTDP-4-dehydro-6-deoxy-D-glucose + NADPH
dTDP-beta-L-rhamnose + NADP+
show the reaction diagram
Q9LQ04
-
-
-
?
dTDP-4-dehydro-6-deoxy-D-glucose + NADPH + H+
dTDP-L-rhamnose + NADP+
show the reaction diagram
-
-
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NAD(P)H
dTDP-L-rhamnose + NAD(P)+
show the reaction diagram
-
-
-
r
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
show the reaction diagram
-
-
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
show the reaction diagram
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
show the reaction diagram
Aggregatibacter actinomycetemcomitans NCTC 9710
-
-
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
show the reaction diagram
-
-
-
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
show the reaction diagram
-
-
-
-
?
UDP-4-dehydro-6-deoxy-D-glucose + NADPH
UDP-beta-L-rhamnose + NADP+
show the reaction diagram
Q9LQ04
-
-
-
?
UDP-4-keto-6-deoxy-D-glucose + NADPH + H+
UDP-L-rhamnose + NADP+
show the reaction diagram
E3VXL5
-
product identification by electrospray ionization-mass spectrometry and gas chromatography mass spectrometry
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
show the reaction diagram
-
biosynthetic pathway, overview
-
-
?
additional information
?
-
Q9LQ04
no substrate: GDP-4-keto-6-deoxy-mannose, UDP-glucose, dTDP-glucose, UDP-xylose, GDP-fucose
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
dTDP-6-deoxy-L-lyxo-4-hexulose + NADPH
dTDP-L-rhamnose + NADP+
show the reaction diagram
-
synthesis of L-rhamnose precurser dTDP-L-rhamnose, essential cell wall component of pathogenic bacteria
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
show the reaction diagram
-
-
-
-
?
dTDP-6-deoxy-L-mannose + NADP+
dTDP-4-dehydro-6-deoxy-L-mannose + NADPH
show the reaction diagram
-
biosynthetic pathway, overview
-
-
?
METALS and IONS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
Mg2+
-
situated at dimer interface
additional information
E3VXL5
divalent metal ions do not alter activity
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
2,6,7-trihydroxy-9-(2-hydroxyphenyl)-3H-xanthen-3-one
-
-
2,6,7-trihydroxy-9-methyl-3H-xanthen-3-one
-
-
2,6,7-trihydroxy-9-phenyl-3H-xanthen-3-one
-
-
5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol
-
-
EDTA
-
up to 0.3 mM, 70% loss of enzyme activity
additional information
-
full activity restored with up to 0.3 mM MgCl2
-
additional information
Q9LQ04
not inhibitory: MgCl2, CaCl2, EDTA at 10mM
-
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0169
-
dTDP-4-keto-6-deoxy-D-glucose
Q9LQ04
pH 8.5, 30C
0.106
-
NADH
-
+/-0.018, pH 7.0
0.21
-
NADH
-
+/-0.004, pH 7.0
0.009
-
NADPH
Q9LQ04
pH 8.5, 30C
1.83
-
UDP-4-keto-6-deoxy-D-glucose
E3VXL5
25C, pH 7.5
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
25
-
NADH
-
+/-48
29
-
NADPH
-
+/-66
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0021
-
2,6,7-trihydroxy-9-(2-hydroxyphenyl)-3H-xanthen-3-one
-
pH and temperature not specified in the publication
0.0015
-
2,6,7-trihydroxy-9-methyl-3H-xanthen-3-one
-
pH and temperature not specified in the publication
0.0009
-
2,6,7-trihydroxy-9-phenyl-3H-xanthen-3-one
-
pH and temperature not specified in the publication
0.0025
-
5-ethenyl-1-methyl-9,10-dihydrophenanthrene-2,7-diol
-
pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
SPECIFIC ACTIVITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
0.0011
-
E3VXL5
25C, pH 7.5
pH OPTIMUM
pH MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
6.5
-
-
reduction of dTDP-6-deoxy-L-lyxo-4-hexulose
7.8
-
-
assay at
10
-
-
oxidation of dTDP-L-rhamnose
pH RANGE
pH RANGE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
5.5
7.5
Q9LQ04
-
TEMPERATURE OPTIMUM
TEMPERATURE OPTIMUM MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-
assay at
TEMPERATURE RANGE
TEMPERATURE MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
45
-
Q9LQ04
about 35% of maximum activity
SOURCE TISSUE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
SOURCE
additional information
Q9LQ04
present in all tissues examined
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Salmonella typhimurium (strain LT2 / SGSC1412 / ATCC 700720)
Sulfolobus tokodaii (strain DSM 16993 / JCM 10545 / NBRC 100140 / 7)
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
31900
-
-
Y4 rmlD gene product, SDS-PAGE
32400
-
-
NCTC 9710 rmlD gene product, SDS-PAGE
32500
-
-
HPLC
32540
-
-
mass spectrometry, native protein
32560
-
-
deduced from sequence
32600
-
-
calculated from nucleotide sequence data
32730
-
-
mass spectrometry, selenomethionine-enriched protein
34800
-
-
SDS-PAGE
41500
-
-
gel filtration
47000
-
E3VXL5
gel filtration
49500
-
-
light-scattering
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
?
Q9LQ04
x * 35500, deduced from gene sequence, x * 35000, SDS-PAGE
monomer or dimer
E3VXL5
x * 33000, UGER, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
apo-enzyme, and in complex with NADH, NADPH or NADPH/dTDP-L-rhamnose
-
sitting drop vapour-diffusion method, 6 d
-
pH STABILITY
pH STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
7
-
-
37C, 20 min, 75% activity loss
TEMPERATURE STABILITY
TEMPERATURE STABILITY MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
30
-
-
stable below
37
-
-
pH 7.0, 75% activity loss
42
-
E3VXL5
stable for 30 min
50
-
-
NADPH more than NADP+ prevents heat denaturation during 5 and 8 min
GENERAL STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
NADPH and to a lesser degree NADP+ prevent denaturation at 50C, NAD+ and NADH are less effective
-
STORAGE STABILITY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
-20C, purified protein, 50% glycerol
-
-20C, repeated freezing and thawing, loss of more than 60% of activity
Q9LQ04
-20C, 44% glycerol
-
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
recombinant enzyme
Q9LQ04
ammonium sulfate precipitation, affinity chromatography, co-purification of enzyme I and II
-
affinity and ion exchange chromatography
-
anion-exchange, hydrophobic chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
gene L780, transcription profiling of UGER, phylogenetic analysis
E3VXL5
overexpression in Escherichia coli DH5alpha, ER2566, BL21(DE3)
-
expression in Escherichia coli
-
gene rmlD, expression in Escherichia coli strain BL21(DE3)
-
native overexpressed in Escherichia coli BL21(DE3) and selenomethionine-enriched in B834(lambdaDE3)
-
overexpressed in Escherichia coli BL21(lambdaDE3)
-
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
synthesis
-
six enzymes, including the dTDP-4-keto-rhamnose reductase, are involved in the pathway and are prepared by recombinant expression in Escherichia coli for large scale production of O-antigen precursor sTDP-L-rhamnose in a one-pot reaction, overview
synthesis
-
development and evaluation of a modular system for large scale production of important dTDP-activated deoxyhexoses from dTMP and sucrose, overview