Information on EC 5.4.99.9 - UDP-galactopyranose mutase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY
5.4.99.9
-
RECOMMENDED NAME
GeneOntology No.
UDP-galactopyranose mutase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
UDP-alpha-D-galactopyranose = UDP-alpha-D-galactofuranose
show the reaction diagram
-
-
-
-
UDP-alpha-D-galactopyranose = UDP-alpha-D-galactofuranose
show the reaction diagram
mobile loop of enzyme must move in order for enzyme to bind UDP-galactose substrate
-
REACTION TYPE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
group transfer
-
-
intramolecular
-
isomerization
-
-
-
-
isomerization
-
-
PATHWAY
KEGG Link
MetaCyc Link
Galactose metabolism
-
mycolyl-arabinogalactan-peptidoglycan complex biosynthesis
-
O-antigen building blocks biosynthesis (E. coli)
-
superpathway of UDP-glucose-derived O-antigen building blocks biosynthesis
-
SYSTEMATIC NAME
IUBMB Comments
UDP-D-galactopyranose furanomutase
A flavoenzyme which generates UDP-alpha-D-glactofuranose required for cell wall formation in bacteria, fungi, and protozoa.
SYNONYMS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
galactopyranose mutase
Q9RYF1
-
GLF gene product
-
-
GLF gene product
Q5KEL8
-
GLF gene product
Q5EEK0
-
GLF gene product
Q5EEK1
-
GLF-1
Caenorhabditis elegans N2
-
-
-
Mutase, uridine diphosphogalactopyranose
-
-
-
-
UDP-D-galactopyranose mutase
-
-
UDP-Gal mutase
-
-
UDP-galactopyranose mutase
-
-
-
-
UDP-galactopyranose mutase
Q4W1X2
-
UDP-galactopyranose mutase
-
-
UDP-galactopyranose mutase
Q5KEL8
-
UDP-galactopyranose mutase
-
-
UDP-galactopyranose mutase
-
-
UDP-galactopyranose mutase
Q5EEK0
-
UDP-galactopyranose mutase
-
-
UDP-galactopyranose mutase
Q5EEK1
-
UDP-Galp mutase
-
-
UGM
Q4W1X2
the key enzyme of galactofuranose metabolism controls the biosynthesis of galactomannan and galactofuranose containing glycoconjugates
UGM
Caenorhabditis elegans N2
-
-
-
UGM
Campylobacter jejuni 11168
-
-
-
UGM
Q5EEK1
-
UgmA
Aspergillus niger RD6.13
-
-
-
UNGM
-
Campylobacter jejuni UNGM has UGM activity in Escherichia coli
UNGM
Campylobacter jejuni 11168
-
Campylobacter jejuni UNGM has UGM activity in Escherichia coli
-
uridine 5'-diphosphate galactopyranose mutase
-
-
uridine 5'-diphosphate galactopyranosemutase
Q48485
-
CAS REGISTRY NUMBER
COMMENTARY
174632-18-9
-
GENERAL INFORMATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
malfunction
-
glf-1 mutants display significant late embryonic and larval lethality, and other phenotypes indicative of defective surface coat synthesis, the glycan-rich outermost layer of the nematode cuticle
malfunction
-
Aspergillus nidulans strains deleted for UgmA lack immunolocalizable UDP-D-galactofuranose, have growth and sporulation defects, abnormal wall architecture, and significantly larger hyphal surface subunits and lower cell wall viscoelastic moduli
malfunction
Caenorhabditis elegans N2
-
glf-1 mutants display significant late embryonic and larval lethality, and other phenotypes indicative of defective surface coat synthesis, the glycan-rich outermost layer of the nematode cuticle
-
physiological function
-
glf-1 is required for normal post-embryonic development
physiological function
-
UDP-galactopyranose mutase is a virulence factor in Leishmania major
physiological function
-
UgmA is important for cell wall surface subunit organization and wall viscoelasticity
physiological function
Caenorhabditis elegans N2
-
glf-1 is required for normal post-embryonic development
-
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
UDP-(6-deoxy-6-fluoro)-D-galactofuranose
UDP-(6-deoxy-6-fluoro)-D-galactopyranose
show the reaction diagram
-
-
-
-
r
UDP-(6-deoxy-6-fluoro)-D-galactofuranose
?
show the reaction diagram
-
-
-
-
?
UDP-2-amino-2-deoxy-D-galactopyranose
?
show the reaction diagram
-
-
-
-
?
UDP-2-deoxy-2-fluoro-D-galactofuranose
?
show the reaction diagram
-
-
-
-
?
UDP-2-deoxy-2-fluoro-D-galactopyranose
?
show the reaction diagram
-
-
-
-
?
UDP-2-fluoro-galactofuranose
?
show the reaction diagram
-
-
-
-
?
UDP-3''-deoxy-3''-fluoro-D-galactopyranose
UDP-3''-deoxy-3''-fluoro-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-3-deoxy-3-fluoro-D-galactofuranose
?
show the reaction diagram
-
-
-
-
?
UDP-3-deoxy-3-fluoro-D-galactofuranose
?
show the reaction diagram
-
-
-
-
?
UDP-3-deoxy-3-fluoro-D-galactopyranose
?
show the reaction diagram
-
-
-
-
?
UDP-6-deoxy-6-fluoro-D-galactopyranose
?
show the reaction diagram
-
-
-
-
?
UDP-6-deoxy-D-galactopyranose
?
show the reaction diagram
-
-
-
-
?
UDP-alpha-D-galactopyranose
UDP-alpha-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-alpha-D-galactopyranose
UDP-alpha-D-galactofuranose
show the reaction diagram
Q9RYF1
-
-
-
r
UDP-beta-L-arabinofuranose
?
show the reaction diagram
-
-
-
-
?
UDP-D-galactofuranose
UDP-D-galactopyranose
show the reaction diagram
-
-
-
-
r
UDP-D-galactofuranose
UDP-D-galactopyranose
show the reaction diagram
-
-
-
-
r
UDP-D-galactofuranose
UDP-D-galactopyranose
show the reaction diagram
-
-
-
-
r
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
r
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
?
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-, Q48485
-
-
-
?
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactofuranose
UDP-galactopyranose
show the reaction diagram
-
-
8-5% product yield, 92-95% product yield
-
r
UDP-galactofuranose
UDP-galactopyranose
show the reaction diagram
Caenorhabditis elegans N2
-
-
8-5% product yield, 92-95% product yield
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-, P37747
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5KEL8
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5EEK0
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-, Q4W1X2
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5EEK1
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q48485
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
essential step of mycobacterial cell wall biosynthesis
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
pH 7.1, 30C
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5KEL8
pH 7.1, 30C
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
pH 7.1, 30C
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5EEK1
pH 7.1, 30C
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Aspergillus niger RD6.13
-
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Campylobacter jejuni 11168
-
-
-
-
?
UDP-L-arabinofuranose
?
show the reaction diagram
-
-
-
-
?
Uridine 5'-(trihydrogen diphosphate) P'-alpha-D-galactopyranosyl ester
Uridine 5'-(trihydrogen diphosphate) P'-alpha-D-galactofuranosyl ester
show the reaction diagram
-
-
-
-
2-fluoro-deoxy-UDP-galactopyranose
2-fluoro-deoxy-UDP-galactofuranose
show the reaction diagram
-
-
-
?
additional information
?
-
-
1,4-anhydrogalactopyranose does not react with UGM and UDP to form UDP-galactopyranose or UDP-galactofuranose
-
-
-
additional information
?
-
-
UDP-galactopyranose mutase as an important protein in fungal cell wall biosynthesis
-
-
-
additional information
?
-
-
no activity with UDP-6-deoxy-Dgalactopyranose, UDP-2-azido-2-deoxy-D-galactopyranose, and UDP-2-acetamido-2-deoxy-D-galactopyranose
-
-
-
additional information
?
-
-
UDP-D-glucose is not a substrate for UGM
-
-
-
additional information
?
-
-
UGM does not interconvert UDP-GalpNAc and UDP-GalfNAc
-
-
-
additional information
?
-
-
the enzyme is active in the oxidized state, being 2-3fold less active than in the reduced state. In the oxidized state, UGM does not bind UDP-galactopyranose
-
-
-
additional information
?
-
-
the enzyme is active only in the reduced state
-
-
-
additional information
?
-
Aspergillus niger RD6.13
-
UDP-galactopyranose mutase as an important protein in fungal cell wall biosynthesis
-
-
-
additional information
?
-
Campylobacter jejuni 11168
-
UGM does not interconvert UDP-GalpNAc and UDP-GalfNAc
-
-
-
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
UDP-D-galactopyranose
UDP-D-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-, P37747
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
?
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5KEL8
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5EEK0
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-, Q4W1X2
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
Q5EEK1
-
-
-
r
UDP-galactopyranose
UDP-galactofuranose
show the reaction diagram
-
essential step of mycobacterial cell wall biosynthesis
-
-
r
COFACTOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
FAD
-
0.52 mol bound FAD per monomer
FAD
-
exists in a reduced state when the enzyme is catalytically active
FAD
-
UGM is only catalytically active when the flavin is in the reduced form
FAD
Q48485
FAD-containing enzyme
FAD
-
flavoenzyme, activity depends on FAD redox state
NAD(P)H
P37747
or other reductants
NAD(P)H
-
or other reductants
NADH
-
or NADPH required
NADPH
-
or NADH required
INHIBITORS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
(1R,3S,4R,7R,8S)-3-hydroxymethyl-2,6-dioxa-bicyclo-[2.2.2]-octane-7,8-diol
-
17% inhibition at 4 mM
(2R,3S,4S,5S,2'R,3'S,4'S,5'S)-2,2'-butane-1,4-diylbis[5-[(1S)-1,2-dihydroxyethyl]-3,4-dihydroxypyrrolidinium] dichloride
-
-
(2S,3S,4S,5R)-2-[(1S)-1,2-dihydroxyethyl]-5-propylpyrrolidine-3,4-diol
-
-
(2S,3S,4S,5R)-2-[(1S)-1,2-dihydroxyethyl]-5-[(1E)-prop-1-en-1-yl]pyrrolidine-3,4-diol
-
-
(2Z)-2-(2-chloro-4-hydroxy-5-nitrobenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
-
comparison with inhibition of Mycobacterium tuberculosis enzyme; dissociation constant 0.0053 mM, comparison with inhibition of Klebsiella pneumoniae enzyme
(4-chlorophenyl)-[1-(4-chlorophenyl)-3-hydroxy-5-methyl-1H-pyrazol-4-yl]-methanone
-
-
-
(4E)-4-(4-chloro-3-nitrobenzylidene)-1-(3,4-dichlorophenyl)pyrazolidine-3,5-dione
-
comparison with inhibition of Mycobacterium tuberculosis enzyme; dissociation constant 0.0049 mM, comparison with inhibition of Klebsiella pneumoniae enzyme
1(R)-1,4-dideoxy-1-C-3-[(ethyl)(uridin-5'-yl)phosphono]-2-propen-1-yl-1,4-imino-D-galactitol
-
25 mM, 52% residual activity
1(R)-1,4-dideoxy-1-C-3-[(uridin-5'-yl)phosphono]-2-propen-1-yl-1,4-imino-D-galactitol
-
2.5 mM, 43% residual activity
1(R)-1-C-allyl-1,4-dideoxy-1,4-imino-D-galactitol
-
25 mM, 61% residual activity
1,4-anhydro-beta-D-galactopyranose (1,5-anhydro-alpha-D-galactofuranose)
-
15% inhibition at 4 mM
1,4-bis-[1(R)-1,4-dideoxy-1,4-imino-D-galactit-1-yl]-2-butene
-
2.5 mM, 50% residual activity
2-(([2-(4-bromophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl]carbonyl)amino)benzoic acid
-
comparison with inhibition of Mycobacterium tuberculosis enzyme
2-[(5E)-5-(3-bromobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
-
comparison with inhibition of Mycobacterium tuberculosis enzyme; dissociation constant 0.0094 mM, comparison with inhibition of Klebsiella pneumoniae enzyme
2-[(5E)-5-(4-bromobenzylidene)-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
-
dissociation constant 0.0093 mM, comparison with inhibition of Klebsiella pneumoniae enzyme
2-[(5Z)-5-[(3-chlorophenyl)methylidene]-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
-
-
2-[5-(3-bromo-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-3-phenyl-propionic acid
-
-
2-[[2-(4-bromo-phenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carbonyl]-amino]-benzoic acid
-
-
2-[[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]amino]-3-(3-iodophenyl)propanoic acid
-
-
3-(4-iodophenyl)-2-[4-(3,4-dichlorophenyl)-thiazol-2-ylamino]-propionic acid
-
-
-
N-(4-[4-[8-([[3-carboxy-4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]carbamothioyl]amino)octyl]phenyl]-2,3-dihydro-1,3-thiazol-2-yl)-4-chlorophenylalanine
-
-
N-[4-oxo-5-(2-oxo-1,2-dihydro-indol-3-ylidene)-thiazolidin-2-ylidene]-benzenesulfonamide
-
-
Sodium borohydride
-
-
Sodium cyanoborohydride
-
-
UDP-(1(1')E)-1_-fluoro-exo-glycal-D-galactofuranose
-
less than 10% inhibition at 1 mM. Time-dependent inactivation proceeds via two-electron processes
UDP-(1(1')Z)-1'-fluoro-exo-glycal-D-galactofuranose
-
less than 10% inhibition at 1 mM. Time-dependent inactivation proceeds via two-electron processes
UDP-C-alpha-D-galactofuranose
-
91% inhibition at 1 mM
UDP-C-alpha-D-galactopyranose
-
36% inhibition at 1 mM
UDP-C-beta-D-galactopyranose
-
8% inhibition at 1 mM
UDP-CH2-Galp
-, Q9RYF1
moderate inhibition of UGM
UDP-CH2-Galp
-
moderate inhibition of UGM
UDP-D-glucose
-
poor inhibitor of UGM
UDP-[1(1')Z]-exo-glycal-D-galactopyranose
-
42% inhibition at 1 mM
uridine diphosphate
-
-
uridine-5'-diphospho-(N-fluoresceinisothiocyano)hexanolamine
-
-
additional information
-
fluorinated substrate analogues under non-reducing conditions
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
5-Deazariboflavin
-
specific activity 29fold higher than of control without illumination
Sodium dithionite
-
20 mM
KM VALUE [mM]
KM VALUE [mM] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
24
-
UDP-(6-deoxy-6-fluoro)-D-galactofuranose
-
-
24
-
UDP-(6-deoxy-6-fluoro)-D-galactofuranose
-
-
1.14
-
UDP-2-amino-2-deoxy-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.065
-
UDP-2-deoxy-2-fluoro-D-galactofuranose
-
-
0.203
-
UDP-2-deoxy-2-fluoro-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.065
-
UDP-2-fluoro-galactofuranose
-
-
0.861
-
UDP-3-deoxy-3-fluoro-D-galactofuranose
-
-
0.861
-
UDP-3-deoxy-3-fluoro-D-galactofuranose
-
-
0.28
-
UDP-3-deoxy-3-fluoro-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.2
-
UDP-6-deoxy-6-fluoro-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
3.15
-
UDP-6-deoxy-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.016
-
UDP-D-galactofuranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.022
-
UDP-D-galactofuranose
-
37C, pH 7.5, in presence of 20 mM sodium dithionite
0.087
-
UDP-D-galactofuranose
-
in 25 mM HEPES, 125 mM NaCl, 20 mM dithionite, pH 7.5, at 37C
0.11
-
UDP-D-galactofuranose
-
in 25 mM HEPES, 125 mM NaCl, 20 mM dithionite, pH 7.5, at 37C
0.194
-
UDP-D-galactofuranose
-
37C, pH 7.5
0.043
-
UDP-D-galactopyranose
-
wild-type, pH 8.0
0.205
-
UDP-D-galactopyranose
-
mutant E301A, pH 8.0
0.386
-
UDP-D-galactopyranose
-
mutant Y185F, pH 8.0
0.619
-
UDP-D-galactopyranose
-
mutant Y155F, pH 8.0
0.739
-
UDP-D-galactopyranose
-
mutant Y349F, pH 8.0
0.805
-
UDP-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.819
-
UDP-D-galactopyranose
-
mutant Y314F, pH 8.0
1.002
-
UDP-D-galactopyranose
-
mutant D351A, pH 8.0
0.02
-
UDP-galactofuranose
-
under reducing conditions
0.022
-
UDP-galactofuranose
-
-
0.19
-
UDP-galactofuranose
-
under non-reducing (native) conditions
0.022
-
UDP-galactopyranose
-
-
0.055
-
UDP-galactopyranose
-
wild type enzyme, in 50 mM sodium phosphate buffer pH 7.0
0.6
-
UDP-L-arabinofuranose
-
-
TURNOVER NUMBER [1/s]
TURNOVER NUMBER MAXIMUM[1/s]
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
7.4
-
UDP-(6-deoxy-6-fluoro)-D-galactofuranose
-
-
7.4
-
UDP-(6-deoxy-6-fluoro)-D-galactofuranose
-
-
1.4
-
UDP-2-amino-2-deoxy-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.033
-
UDP-2-deoxy-2-fluoro-D-galactofuranose
-
-
0.0007
-
UDP-2-deoxy-2-fluoro-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
0.033
-
UDP-2-fluoro-galactofuranose
-
-
5.7
-
UDP-3-deoxy-3-fluoro-D-galactofuranose
-
-
5.7
-
UDP-3-deoxy-3-fluoro-D-galactofuranose
-
-
0.9
-
UDP-3-deoxy-3-fluoro-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
3.5
-
UDP-6-deoxy-6-fluoro-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
42.2
-
UDP-6-deoxy-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
1.5
-
UDP-D-galactofuranose
-
37C, pH 7.5
5
-
UDP-D-galactofuranose
-
in 25 mM HEPES, 125 mM NaCl, 20 mM dithionite, pH 7.5, at 37C
27
-
UDP-D-galactofuranose
-
37C, pH 7.5, in presence of 20 mM sodium dithionite
36.8
-
UDP-D-galactofuranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
72
-
UDP-D-galactofuranose
-
in 25 mM HEPES, 125 mM NaCl, 20 mM dithionite, pH 7.5, at 37C
0.13
-
UDP-D-galactopyranose
-
mutant D351A, pH 8.0
0.3
-
UDP-D-galactopyranose
-
mutant E301A, pH 8.0
1.3
-
UDP-D-galactopyranose
-
mutant Y185F, pH 8.0
1.7
-
UDP-D-galactopyranose
-
mutant Y349F, pH 8.0
3.6
-
UDP-D-galactopyranose
-
mutant Y155F, pH 8.0
5.2
-
UDP-D-galactopyranose
-
mutant Y314F, pH 8.0
5.5
-
UDP-D-galactopyranose
-
wild-type, pH 8.0
35.3
-
UDP-D-galactopyranose
-
in 50 mM MOPS, 10 mM sodium dithionite, 2 mM MgCl2 pH 7.4, at 37C
27
-
UDP-galactofuranose
-
-
27
-
UDP-galactopyranose
-
-
66
-
UDP-galactopyranose
-
wild type enzyme, in 50 mM sodium phosphate buffer pH 7.0
12
-
UDP-L-arabinofuranose
-
-
kcat/KM VALUE [1/mMs-1]
kcat/KM VALUE [1/mMs-1] Maximum
SUBSTRATE
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.34
-
UDP-(6-deoxy-6-fluoro)-D-galactofuranose
-
-
271999
0.41
-
UDP-2-fluoro-galactofuranose
-
-
293341
57
-
UDP-D-galactofuranose
-
in 25 mM HEPES, 125 mM NaCl, 20 mM dithionite, pH 7.5, at 37C
206565
650
-
UDP-D-galactofuranose
-
in 25 mM HEPES, 125 mM NaCl, 20 mM dithionite, pH 7.5, at 37C
206565
1230
-
UDP-galactofuranose
-
-
17637
1180
-
UDP-galactopyranose
-
wild type enzyme, in 50 mM sodium phosphate buffer pH 7.0
17638
Ki VALUE [mM]
Ki VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.0016
-
2-[5-(3-bromo-benzylidene)-4-oxo-2-thioxo-thiazolidin-3-yl]-3-phenyl-propionic acid
-
-
0.0046
-
2-[[2-(4-bromo-phenyl)-1,3-dioxo-2,3-dihydro-1H-isoindole-5-carbonyl]-amino]-benzoic acid
-
-
0.017
-
N-[4-oxo-5-(2-oxo-1,2-dihydro-indol-3-ylidene)-thiazolidin-2-ylidene]-benzenesulfonamide
-
-
0.0013
-
uridine-5'-diphospho-(N-fluoresceinisothiocyano)hexanolamine
-
-
IC50 VALUE [mM]
IC50 VALUE [mM] Maximum
INHIBITOR
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
IMAGE
0.004
-
(2Z)-2-(2-chloro-4-hydroxy-5-nitrobenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
-
pH 7.0, 37C
0.035
-
(2Z)-2-(2-chloro-4-hydroxy-5-nitrobenzylidene)[1,3]thiazolo[3,2-a]benzimidazol-3(2H)-one
-
pH 7.0, 37C
0.044
-
(4-chlorophenyl)-[1-(4-chlorophenyl)-3-hydroxy-5-methyl-1H-pyrazol-4-yl]-methanone
-
pH and temperature not specified in the publication
-
0.062
-
(4-chlorophenyl)-[1-(4-chlorophenyl)-3-hydroxy-5-methyl-1H-pyrazol-4-yl]-methanone
-
pH and temperature not specified in the publication
-
0.004
-
(4E)-4-(4-chloro-3-nitrobenzylidene)-1-(3,4-dichlorophenyl)pyrazolidine-3,5-dione
-
pH 7.0, 37C
0.041
-
(4E)-4-(4-chloro-3-nitrobenzylidene)-1-(3,4-dichlorophenyl)pyrazolidine-3,5-dione
-
pH 7.0, 37C
0.0046
-
2-(([2-(4-bromophenyl)-1,3-dioxo-2,3-dihydro-1H-isoindol-5-yl]carbonyl)amino)benzoic acid
-
pH 7.0, 37C
0.0016
-
2-[(5E)-5-(3-bromobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
-
pH 7.0, 37C
0.065
-
2-[(5E)-5-(3-bromobenzylidene)-4-oxo-2-thioxo-1,3-thiazolidin-3-yl]-3-phenylpropanoic acid
-
pH 7.0, 37C
0.0072
-
3-(4-iodophenyl)-2-[4-(3,4-dichlorophenyl)-thiazol-2-ylamino]-propionic acid
-
pH and temperature not specified in the publication
-
0.037
-
3-(4-iodophenyl)-2-[4-(3,4-dichlorophenyl)-thiazol-2-ylamino]-propionic acid
-
pH and temperature not specified in the publication
-
0.0035
-
N-(4-[4-[8-([[3-carboxy-4-(6-hydroxy-3-oxo-3H-xanthen-9-yl)phenyl]carbamothioyl]amino)octyl]phenyl]-2,3-dihydro-1,3-thiazol-2-yl)-4-chlorophenylalanine
-
-
0.411
-
UDP-CH2-Galp
-, Q9RYF1
in 50 mM sodium phosphate buffer (pH 7.0), at 22C
0.479
-
UDP-CH2-Galp
-
in 50 mM sodium phosphate buffer (pH 7.0), at 22C
0.495
-
UDP-CH2-Galp
-
in 50 mM sodium phosphate buffer (pH 7.0), at 22C
PDB
SCOP
CATH
ORGANISM
Campylobacter jejuni subsp. jejuni serotype O:2 (strain NCTC 11168)
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Deinococcus radiodurans (strain ATCC 13939 / DSM 20539 / JCM 16871 / LMG 4051 / NBRC 15346 / NCIMB 9279 / R1 / VKM B-1422)
Escherichia coli (strain K12)
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Neosartorya fumigata
Trypanosoma cruzi (strain CL Brener)
Trypanosoma cruzi (strain CL Brener)
MOLECULAR WEIGHT
MOLECULAR WEIGHT MAXIMUM
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
72000
-
-
gel filtration
92000
-
-
gel filtration
228600
-
-
calculated from amino acid sequence
275000
-
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
dimer
-
2 * 45000, SDS-PAGE
dimer
P37747
solution scattering experiments
dimer
-
alpha2, crystal structure
homodimer
-
alpha2, 2 * 43000, crystallization
homodimer
-
alpha2, 2 * 44000, calculated from translated peptide sequence
homotetramer
-
4 * 55000, SDS-PAGE; 4 * 57152, calculated from amino acid sequence
monomer
-
1 * 54960, calculated from amino acid sequence; 1 * 55000, SDS-PAGE
Crystallization/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
in complex with UDP-CH2-Galp, hanging drop vapor diffusion method, using 0.1 M HEPES (pH 6.5), 0.2 M LiCl, and 28% (w/v) polyethylene glycol 6000
-, Q9RYF1
in complex with UDP-galactopyranose and UDP and uridine diphosphate, microbatch under oil method, using 0.1 M HEPES, pH 6.5, 0.2 M lithium chloride and 28% (w/v) PEG 6000
-
in complex with UDP-galactopyranose, microbatch-under-oil method, using 0.1 M HEPES pH 7.0, 0.2 M LiCl, and 20% (w/v) PEG 6000
-
FAD is located in a cleft lined with conserved residues
P37747
vapour-diffusion method in hanging drops, orthorhombic, space group P21 with a: 71.12 A, b: 58.42 A, c: 96.38 A, beta: 96.38
-
in complex with UDP-D-glucose
-
in the (active) reduced state, with FAD, crystal structure at 2.2 A resolution, with FADH-, crystal structure at 2.25 A resolution
-
in the oxidized state, with FAD, crystal structure at 2.25 A resolution
-
substrate-bound enzyme in oxidized and reduced forms
Q48485
Purification/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
nickel immobilized affinity chromatography and DEAE column chromatography
-
HQ20 column chromatography and HP-20 column chromatography
-
HQ20 column chromatography and HP-20 hydrophobic interaction chromatography column
-
Protino Ni-IDA 1000 column chromatography
-, Q9RYF1
Protino Ni-IDA 1000 column chromatography
-
the recombinant enzyme
-
the recombinant enzyme from Escherichia coli
-
nickel immobilized metal affinity chromatography, DEAE column chromatography, and purification with HaloLink resin
-
Protino Ni-IDA 1000 column chromatography
-
the recombinant enzyme from Escherichia coli
-
Cloned/COMMENTARY
ORGANISM
UNIPROT ACCESSION NO.
LITERATURE
expressed in Escherichia coli
-
expressed in Escherichia coli BL21T1 cells
-
expression in Escherichia coli
-
expressed in Escherichia coli DH5alpha cell
-
expression in Escherichia coli
-
expressed in Escherichia coli strain strain MFF1
-
expression in Escherichia coli
Q5KEL8
expressed in Escherichia coli C43 cells
-, Q9RYF1
expressed in Escherichia coli Tuner cells
-
expression in Escherichia coli with a His-tag
-
overexpression in Escherichia coli
P37747
expressed in Escherichia coli
-
expressed in Escherichia coli C43 cells
-
expression in Escherichia coli (ER2566)
-
expression in Escherichia coli with a His-tag
-
expression in Escherichia coli, His-tagged protein
-
expression with His-tag in Escherichai coli
-
overexpression in Escherichia coli
-
expressed in Escherichia coli BL21T1 and BL21(DE3) cells
-
expression in Escherichia coli
Q5EEK0
expressed in Escherichia coli C43 cells
-
expression in Escherichia coli (BL21(DE3))
-
expression in Escherichia coli
Q5EEK1
ENGINEERING
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
D351A
-
mutation of conserved residue of putative active site cleft. 4% of wild-type activity
E301A
-
mutation of conserved residue of putative active site cleft. 21% of wild-type activity
R174A
-
no catalytic activity
R280A
-
mutation of conserved residue of putative active site cleft. No catalytic activity
W156A
-
lower activity than wild-type enzyme
W156Y
-
lower activity than wild-type enzyme
W160A
-
mutation of conserved residue on edge putative active site cleft, defective in binding of substrate
W160A
-
catalytically inert
W160A
-
redox-switched binding affinity of substrate reverses in the W160A mutant where it only binds when oxidized
W70F/W290F
-
wild type UGM and the W70F/W290F double mutant show competition of UDP and UDP-galactopyranose for the same site
W70F/W290F
-
the double mutant binds substrate in a similar manner to wild type and has comparable enzyme activity (90%)
Y151F
-
lower activity than wild-type enzyme
Y155F
-
7% of wild-type activity
Y181F
-
lower activity than wild-type enzyme
Y185F
-
11% of wild-type activity
Y311F
-
lower activity than wild-type enzyme
Y314F
-
5% of wild-type activity
Y346F
-
lower activity than wild-type enzyme
additional information
-
compared to a wild type morphology strain, the UGM-deficient ugmA? strain has aberrant hyphal morphology, producing wide, uneven, highly-branched hyphae, with thick, relatively electron-dense walls
Y349F
-
6% of wild-type activity
additional information
-
gene replacement mutant is deficient in lipophosphoglycan backbone and expresses truncated glycoinositolphospholipids. The structural changes do not influence the in vitro growth but lead to an attenuation of virulence
APPLICATION
ORGANISM
UNIPROT ACCESSION NO.
COMMENTARY
LITERATURE
drug development
-
the product galactofuranose is valued as an important target for the development of new antituberculosis drugs
medicine
-
the UDP-galactopyranose mutase is an appealing adjunct therapeutic target in combination with other drugs against Aspergillus fumigatus
drug development
-
UGM inhibition may provide an attractive drug target in those eukaryotes where galactofuranose plays a critical role in cellular viability and virulence
drug development
Q5KEL8
UGM inhibition may provide an attractive drug target in those eukaryotes where galactofuranose plays a critical role in cellular viability and virulence
analysis
-
high-throughput fluorescence polarization assay for indentification of inhibitors of enzyme and homologues
drug development
-
blocking the incorporation of the product galactofuranose into polysaccharides essential for pathogen viability or virulence may lead to novel therapeutics
synthesis
-
production of uridine 5'-(trihydrogen diphosphate) P'-alpha-D-galactofuranosyl ester, a precursor required for the formation of the lipopolysaccharide O-antigen of Klebsiella pneumoniae serotype O1
drug development
-
the product galactofuranose is valued as an important target for the development of new antituberculosis drugs
drug development
-
UGM inhibition may provide an attractive drug target in those eukaryotes where galactofuranose plays a critical role in cellular viability and virulence
drug development
Q5EEK1
UGM inhibition may provide an attractive drug target in those eukaryotes where galactofuranose plays a critical role in cellular viability and virulence