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
LITERATURE
dTDP-beta-L-rhamnose + NADP+ = dTDP-4-dehydro-beta-L-rhamnose + NADPH + H+
show the reaction diagram
the complex has been referred to as dTDP-L-rhamnose synthase, 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
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
-
-
dTDP-L-rhamnose biosynthesis I
-
-
dTDPLrhamnose biosynthesis
-
-
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
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
UNIPROT
SEQUENCE DB
SOURCE
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
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
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
-
-
?
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
-
preferred
NADPH
-
-
NADPH
Q9LQ04
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
-
situated at dimer interface
additional information
E3VXL5
divalent metal ions do not alter activity
INHIBITORS
ORGANISM
UNIPROT
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]
SUBSTRATE
ORGANISM
UNIPROT
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]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
25
NADH
-
+/-48
29
NADPH
-
+/-66
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
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]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0011
E3VXL5
25C, pH 7.5
pH OPTIMUM
ORGANISM
UNIPROT
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
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
5.5 - 7.5
Q9LQ04
-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
45
Q9LQ04
about 35% of maximum activity
SOURCE TISSUE
ORGANISM
UNIPROT
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
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
31900
-
Y4 rmlD gene product, SDS-PAGE
285845
32400
-
NCTC 9710 rmlD gene product, SDS-PAGE
285845
32500
-
HPLC
285844
32540
-
mass spectrometry, native protein
285844
32560
-
deduced from sequence
285844
32600
-
calculated from nucleotide sequence data
285846
32730
-
mass spectrometry, selenomethionine-enriched protein
285844
34800
-
SDS-PAGE
285846
41500
-
gel filtration
285846
47000
E3VXL5
gel filtration
716065
49500
-
light-scattering
285844
SUBUNITS
ORGANISM
UNIPROT
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
LITERATURE
apo-enzyme, and in complex with NADH, NADPH or NADPH/dTDP-L-rhamnose
-
sitting drop vapour-diffusion method, 6 d
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7
-
37C, 20 min, 75% activity loss
285846
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
30
-
stable below
285846
37
-
pH 7.0, 75% activity loss
285846
42
E3VXL5
stable for 30 min
716065
50
-
NADPH more than NADP+ prevents heat denaturation during 5 and 8 min
285843
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
NADPH and to a lesser degree NADP+ prevent denaturation at 50C, NAD+ and NADH are less effective
-
STORAGE STABILITY
ORGANISM
UNIPROT
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
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
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
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