Information on EC 2.7.1.162 - N-acetylhexosamine 1-kinase

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The expected taxonomic range for this enzyme is: Bifidobacterium longum

EC NUMBER
COMMENTARY hide
2.7.1.162
-
RECOMMENDED NAME
GeneOntology No.
N-acetylhexosamine 1-kinase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
ATP + N-acetyl-D-hexosamine = ADP + N-acetyl-alpha-D-hexosamine 1-phosphate
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Phosphorylation
SYSTEMATIC NAME
IUBMB Comments
ATP:N-acetyl-D-hexosamine 1-phosphotransferase
This enzyme is involved in the lacto-N-biose I/galacto-N-biose degradation pathway in the probiotic bacterium Bifidobacterium longum. Differs from EC 2.7.1.157, N-acetylgalactosamine kinase, as it can phosphorylate both N-acetylgalactosamine and N-acetylglucosamine at similar rates. Also has some activity with N-acetyl-D-mannosamine, D-talose and D-mannose as substrate. ATP can be replaced by GTP or ITP but with decreased enzyme activity. Requires a divalent cation, with Mg2+ resulting in by far the greatest stimulation of enzyme activity.
CAS REGISTRY NUMBER
COMMENTARY hide
959459-09-7
protein sequence
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
strain JCM1217
SwissProt
Manually annotated by BRENDA team
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
ATP + 2-(acetylamino)-2-deoxy-D-allopyranose
ADP + 2-(acetylamino)-2-deoxy-D-allopyranose 1-phosphate
show the reaction diagram
22% phosphorylation yield
-
-
?
ATP + 2-deoxy-2-azido-D-mannose
ADP + 2-deoxy-2-azido-alpha-D-mannose 1-phosphate
show the reaction diagram
ATP + 2-deoxy-2-fluoro-D-mannose
ADP + 2-deoxy-2-fluoro-alpha-D-mannose 1-phosphate
show the reaction diagram
ATP + 2-deoxy-D-glucose
ADP + 2-deoxy-alpha-D-glucose 1-phosphate
show the reaction diagram
ATP + 4- deoxy-N-acetyl-D-glucosamine
ADP + 4-deoxy-N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
-
50% phosphorylation yield
-
-
?
ATP + 4-deoxy-4-azido-N-acetyl-D-galactosamine
ADP + 4-deoxy-4-azido-N-acetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
-
73% phosphorylation yield
-
-
?
ATP + 4-deoxy-D-mannose
ADP + 4-deoxy-alpha-D-mannose 1-phosphate
show the reaction diagram
ATP + 6-deoxy-6-azido-N-acetyl-D-galactosamine
ADP + 6-deoxy-6-azido-N-acetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
-
42% phosphorylation yield
-
-
?
ATP + 6-deoxy-6-azido-N-acetyl-D-glucosamine
ADP + 6-deoxy-6-azido-N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
ATP + 6-deoxy-6-methyl-N-acetyl-D-glucosamine
ADP + 6-deoxy-6-methyl-N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
ATP + 6-deoxy-N-acetyl-D-galactosamine
ADP + 6-deoxy-N-acetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
-
37% phosphorylation yield
-
-
?
ATP + 6-deoxy-N-acetyl-D-glucosamine
ADP + 6-deoxy-N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
75% phosphorylation yield
-
-
?
ATP + 6-methyl-N-acetyl-D-mannose
ADP + 6-methyl-N-acetyl-alpha-D-mannose 1-phosphate
show the reaction diagram
ATP + D-galactopyranose
ADP + alpha-D-galactopyranose 1-phosphate
show the reaction diagram
-
below 5% phosphorylation yield
-
-
?
ATP + D-mannose
?
show the reaction diagram
ATP + D-mannose
ADP + alpha-D-mannose 1-phosphate
show the reaction diagram
ATP + D-talose
?
show the reaction diagram
phosphorylation at 3% of the activity with N-acetylglucosamine
-
-
?
ATP + N-acetyl-alpha-D-galactosamine
ADP + N-acetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
ATP + N-acetyl-alpha-D-glucosamine
ADP + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
ATP + N-acetyl-D-galactosamine
ADP + N-acetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
ATP + N-acetyl-D-glucosamine
ADP + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
90% phosphorylation yield
-
-
?
ATP + N-acetyl-D-mannosamine
?
show the reaction diagram
phosphorylation at 15% of the activity with N-acetylglucosamine
-
-
?
ATP + N-acetyl-D-mannosamine
ADP + ?
show the reaction diagram
-
-
-
?
ATP + N-azidoacetyl-D-galactosamine
ADP + N-azidoacetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
-
65% phosphorylation yield
-
-
?
ATP + N-azidoacetyl-D-glucosamine
ADP + N-azidoacetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
87% phosphorylation yield
-
-
?
ATP + N-benzoyl-alpha-D-galactosamine
ADP + N-benzoyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
ATP + N-butanoyl-D-galactosamine
ADP + N-butanoyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
ATP + N-butanoyl-D-glucosamine
ADP + N-butanoyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
ATP + N-phenylacetyl-D-galactosamine
ADP + N-phenylacetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
-
77% phosphorylation yield
-
-
?
ATP + N-phenylacetyl-D-glucosamine
ADP + N-phenylacetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
88% phosphorylation yield
-
-
?
ATP + N-propionyl-D-galactosamine
ADP + N-propionyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
-
85% phosphorylation yield
-
-
?
ATP + N-propionyl-D-glucosamine
ADP + N-propionyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
86% phosphorylation yield
-
-
?
ATP + N-trifluoroacetyl-alpha-D-galactosamine
ADP + N-trifluoroacetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
-
0.75 microM, 21.8% conversion
-
-
?
GTP + N-acetyl-alpha-D-glucosamine
GDP + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
GTP shows about 45% of the activity with ATP
-
-
?
ITP + N-acetyl-alpha-D-glucosamine
IDP + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
ITP shows about 30% of the activity with ATP
-
-
?
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
ATP + N-acetyl-alpha-D-galactosamine
ADP + N-acetyl-alpha-D-galactosamine 1-phosphate
show the reaction diagram
ATP + N-acetyl-alpha-D-glucosamine
ADP + N-acetyl-alpha-D-glucosamine 1-phosphate
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
1 mM, 1% relative activity compared to Mg2+
Co2+
1 mM, 21% relative activity compared to Mg2+; 21% of the activity with Mg2+
MgCl2
-
10 mM are included in the assay medium
Mn2+
1 mM, 7% relative activity compared to Mg2+
Ni2+
1 mM, 4% relative activity compared to Mg2+
Zn2+
1 mM, 8% relative activity compared to Mg2+
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
isopropyl-1-thio-beta-D-galactoside
induction of protein expression at a final concentration of 0.5 mM
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.06 - 0.172
ATP
0.065 - 0.09
N-acetyl-alpha-D-galactosamine
0.06 - 0.118
N-acetyl-alpha-D-glucosamine
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.38 - 1.3
ATP
0.46 - 6.08
N-acetyl-alpha-D-galactosamine
0.95 - 1.21
N-acetyl-alpha-D-glucosamine
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
4.8 - 11.8
ATP
4
5.1 - 7.1
N-acetyl-alpha-D-galactosamine
2057
15.8 - 18.3
N-acetyl-alpha-D-glucosamine
1537
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.001
D-glucose, substrate donor specificity
0.002
D-mannosamine, substrate donor specificity
0.004
D-glucosamine, substrate donor specificity
0.007
2-deoxyglucose, substrate donor specificity
0.024
D-mannose, substrate donor specificity
0.049
D-talose, substrate donor specificity
0.22
N-acetyl-D-mannosamine, substrate donor specificity
0.48
ITP, substrate donor specificity
0.65
GTP, substrate donor specificity
0.89
N-acetyl-D-galactosamine, substrate donor specificity
1.48
ATP, substrate donor specificity
1.49
N-acetyl-D-glucosamine, substrate donor specificity
additional information
Incubation of 4 microM LnpB protein with 10 mM N-acetyl-alpha-D-glucosamine 6-sulfate in 0.1 M MOPS buffer (pH 7.5) at 30C for 30 min shows that the protein have no hydrolytic activity
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Bifidobacterium longum subsp. infantis (strain ATCC 15697 / DSM 20088 / JCM 1222 / NCTC 11817 / S12)
Bifidobacterium longum subsp. infantis (strain ATCC 15697 / DSM 20088 / JCM 1222 / NCTC 11817 / S12)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
Bifidobacterium longum subsp. longum (strain ATCC 15707 / DSM 20219 / JCM 1217 / NCTC 11818 / E194b)
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5 - 9.5
stability at 30C; stable
677700
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
50
pH 8.5, 30 min, 50% loss of activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
loses half of enzyme activity during incubation for 30 min at 50C in 0.1 M Tris buffer (pH 8.5)
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; The transformant is cultivated and protein expression is induced by the addition of isopropyl-1-thio-beta-D-galactoside. The cells are harvested by centrifugation and sonicated. Cell debris is removed by centrifugation and enzyme is purified on an Ni-nitrilotriacetic acid agarose gel.
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Escherichia coli strains select96 and BL21(DE3) are used as hosts for cloning and expression.; expression in Escherichia coli
expression in Escherichia coli
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
synthesis
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an N-acetylhexosamine 1-kinase from Bifidobacterium infantis (NahK_15697), a guanosine 5'-diphosphate (GDP)-mannose pyrophosphorylase from Pyrococcus furiosus (PFManC), and an Escherichia coli inorganic pyrophosphatase (EcPpA) are used efficiently for a one-pot three enzyme synthesis of GDP-mannose, GDP-glucose, their derivatives, and GDP-talose from simple monosaccharides and derivatives in preparative scale