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EC Tree
The taxonomic range for the selected organisms is: Homo sapiens The expected taxonomic range for this enzyme is: Bacteria, Archaea, Eukaryota
Synonyms
dmsas, neu5ac-9-p synthase, n-acetylneuraminic acid phosphate synthase, neunac-9-p synthase, sialic acid 9-phosphate synthase, n-acetylneuraminic acid 9-phosphate synthase, n-acetylneuraminate 9-phosphate synthase,
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N-acetylneuraminate 9-phosphate synthase
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N-acetylneuraminate-9-phosphate lyase
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N-acetylneuraminate-9-phosphate sialic acid 9-phosphate synthase
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N-acetylneuraminate-9-phosphate synthetase
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N-acetylneuraminic acid 9-phosphate synthase
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N-acetylneuraminic acid 9-phosphate synthetase
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N-acetylneuraminic acid phosphate synthase
N-acetylneuraminic acid-9-phosphate synthase
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N-acylneuraminate-9-phosphate pyruvate-lyase (pyruvate-phosphorylating)
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Neu5Ac 9-phosphate synthase
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Neu5Ac 9-phosphate synthetase
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NeuNAc phosphate synthase
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sialic acid 9-phosphate synthase
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N-acetylneuraminic acid phosphate synthase
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N-acetylneuraminic acid phosphate synthase
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NeuNAc-9-P synthase
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SAS
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sialic acid synthase
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condensation
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phosphoenolpyruvate:N-acyl-D-mannosamine-6-phosphate 1-(2-carboxy-2-oxoethyl)transferase
Acts on N-glycoloyl and N-acetyl-derivatives.
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D-mannose 6-phosphate + ?
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D-mannose 6-phosphate + phosphoenolpyruvate + H2O
2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate + phosphate
N-acetyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acetyl-neuraminate 9-phosphate + phosphate
N-acetyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acetylneuraminate 9-phosphate + phosphate
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N-acetyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acetylneuraminic acid 9-phosphate + phosphate
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?
N-acyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acylneuraminate 9-phosphate + phosphate
N-acyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acylneuraminic acid 9-phosphate + phosphate
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?
N-glycolyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-glycolyl-neuraminate 9-phosphate + phosphate
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?
D-mannose 6-phosphate + phosphoenolpyruvate + H2O
2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate + phosphate
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?
D-mannose 6-phosphate + phosphoenolpyruvate + H2O
2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate + phosphate
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?
N-acetyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acetyl-neuraminate 9-phosphate + phosphate
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?
N-acetyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acetyl-neuraminate 9-phosphate + phosphate
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?
N-acyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acylneuraminate 9-phosphate + phosphate
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?
N-acyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acylneuraminate 9-phosphate + phosphate
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?
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N-acetyl-D-mannosamine 6-phosphate + phosphoenolpyruvate + H2O
N-acetyl-neuraminate 9-phosphate + phosphate
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Cd2+
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1 mM, 30% increase of activity
Mn2+
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1 mM, 15% increase of activity
Mn2+
activity is favored by the presence of Mn2+ ions at a concentration of 12.5 mM
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Ba2+
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1 mM, 93% decrease of activity
Ca2+
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1 mM, 76% decrease of activity
Co2+
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1 mM, 15% decrease of activity
Cu2+
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1 mM, 68% decrease of activity
EDTA
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10 mM, complete inhibition
Fe2+
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1 mM, 79% decrease of activity
Mg2+
12.5 mM Mg2+ decrease the ability for N-acetylneuraminate 9-phosphate synthesis by almost half, while the 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate synthetic activity drops by 20%
Ni2+
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1 mM, 24% decrease of activity
Zn2+
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1 mM, 87% decrease of activity
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Sialic Acid Storage Disease
Engineering Sialic Acid Synthesis Ability in Insect Cells.
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2.5 - 5
D-mannose 6-phosphate
1.04 - 1.72
N-acetyl-D-mannosamine 6-phosphate
2.5 - 5
D-mannose 6-phosphate
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mutant enzyme M42L, at 37°C
2.62
D-mannose 6-phosphate
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in 50 mM bicine pH 7.5 at 37°C
2.62
D-mannose 6-phosphate
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wild type enzyme, at 37°C
1.04
N-acetyl-D-mannosamine 6-phosphate
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in 50 mM bicine pH 7.5 at 37°C
1.04
N-acetyl-D-mannosamine 6-phosphate
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wild type enzyme, at 37°C
1.26
N-acetyl-D-mannosamine 6-phosphate
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mutant enzyme M42T, at 37°C
1.72
N-acetyl-D-mannosamine 6-phosphate
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mutant enzyme M42L, at 37°C
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0.008 - 0.67
D-mannose 6-phosphate
0.013 - 1.31
N-acetyl-D-mannosamine 6-phosphate
0.008
D-mannose 6-phosphate
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mutant enzyme M42L, at 37°C
0.011
D-mannose 6-phosphate
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wild type enzyme, at 37°C
0.67
D-mannose 6-phosphate
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in 50 mM bicine pH 7.5 at 37°C
0.013
N-acetyl-D-mannosamine 6-phosphate
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mutant enzyme M42T, at 37°C
0.016
N-acetyl-D-mannosamine 6-phosphate
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mutant enzyme M42L, at 37°C
0.022
N-acetyl-D-mannosamine 6-phosphate
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wild type enzyme, at 37°C
1.31
N-acetyl-D-mannosamine 6-phosphate
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in 50 mM bicine pH 7.5 at 37°C
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0.22
in the presence of 12.5 mM MnCl2, 8.3 mM phosphoenolpyruvate and 12.5 mM D-mannose 6-phosphate
11.7
in the presence of 12.5 mM MnCl2, 8.3 mM phosphoenolpyruvate and 2.5 mM N-acyl-D-mannosamine 6-phosphate
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SwissProt
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SwissProt
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amino acid sequence
SwissProt
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expression in Sf9 system
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human
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brenda
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SIAS_HUMAN
359
0
40308
Swiss-Prot
other Location (Reliability: 2 )
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41000
2 * 41000, gel filtration
43000
2 * 43000, SDS-PAGE
42360
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calculated from sequence of cDNA
42360
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ESI mass spectrometry
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dimer or trimer
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the molecular weight is more than the size of a dimer, but smaller than a trimer
homodimer
2 * 43000, SDS-PAGE
homodimer
2 * 41000, gel filtration
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M42L
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mutant shows the additional 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate synthase activity like the wild type enzyme
M42T
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the mutation abolishes the 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate synthase activity completely without compromising the Neu5Ac-9-P synthase activity
additional information
by replacing the antifreeze-like domain of the human NeuNAc-9-P synthase with the mouse antifreeze-like domain, the chimeric protein retains almost half of the ability of the human enzyme for 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid-9-phosphate synthesis while the N-acetylneuraminate 9-phosphate production is reduced to less than 10%, the chimeric enzyme is less resistant to high temperatures compared to the wild type enzyme
additional information
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by replacing the antifreeze-like domain of the human NeuNAc-9-P synthase with the mouse antifreeze-like domain, the chimeric protein retains almost half of the ability of the human enzyme for 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid-9-phosphate synthesis while the N-acetylneuraminate 9-phosphate production is reduced to less than 10%, the chimeric enzyme is less resistant to high temperatures compared to the wild type enzyme
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37 - 65
the enzyme loses 43% of its initial KDN-9-P synthetic activity after 10 min at 37°C or 55°C, treatment for 10 min at 65°C results in retention of 26% and 39% of N-acetylneuraminate 9-phosphate and 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid-9-phosphate activity respectively
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HisTrap column chromatography and HiTrap SP column chromatography
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Ni2+ chelating Sepharose column chromatography
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Ni2+-Sepharose Fast Flow column chromatography
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expressed in Arabidopsis thaliana
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expressed in Escherichia coli
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expressed in Escherichia coli BL21 cells
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synthesis
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synthesis of CMP-N-acetylneuraminic acid in Sf9 expression system by coexpression of enzyme with UDP-GlcNAc-2-epimerase/ManNAc kinase and CMP-sialic acid synthetase plus addition of N-acetylglucosamine
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Watson, D.; Jourdian, G.W.; Roseman, S.
The sialic acids. VIII. Sialic acid 9-phosphate synthetase
J. Biol. Chem.
241
5627-5636
1966
Ovis aries, Homo sapiens, Rattus norvegicus, Sus scrofa
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Chen, H.; Blume, A.; Zimmermann-Kordmann, M.; Reutter, W.; Hinderlich, S.
Purification and characterization of N-acetylneuraminic acid-9-phosphate synthase from rat liver
Glycobiology
12
65-71
2002
Escherichia coli, Homo sapiens (Q9NR45), Homo sapiens, Rattus norvegicus
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Kim, K.; Lawrence, S.M.; Park, J.; Pitts, L.; Vann, W.F.; Betenbaugh, M.J.; Palter, K.B.
Expression of a functional Drosophila melanogaster N-acetylneuraminic acid (Neu5Ac) phosphate synthase gene: Evidence for endogenous sialic acid biosynthetic ability in insects
Glycobiology
12
73-83
2002
Drosophila melanogaster, Drosophila melanogaster (Q9VG74), Escherichia coli, Homo sapiens (Q9NR45), Homo sapiens
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Viswanathan, K.; Narang, S.; Hinderlich, S.; Lee, Y.C.; Betenbaugh, M.J.
Engineering intracellular CMP-sialic acid metabolism into insect cells and methods to enhance its generation
Biochemistry
44
7526-7534
2005
Homo sapiens
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Gulesserian, T.; Engidawork, E.; Fountoulakis, M.; Lubec, G.
Manifold decrease of sialic acid synthase in fetal Down syndrome brain
Amino Acids
32
141-144
2007
Homo sapiens (Q9NR45)
brenda
Hao, J.; Balagurumoorthy, P.; Sarilla, S.; Sundaramoorthy, M.
Cloning, expression, and characterization of sialic acid synthases
Biochem. Biophys. Res. Commun.
338
1507-1514
2005
Homo sapiens
brenda
Go, S.; Sato, C.; Yin, J.; Kannagi, R.; Kitajima, K.
Hypoxia-enhanced expression of free deaminoneuraminic acid in human cancer cells
Biochem. Biophys. Res. Commun.
357
537-542
2007
Homo sapiens
brenda
Hao, J.; Vann, W.F.; Hinderlich, S.; Sundaramoorthy, M.
Elimination of 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate synthase activity from human N-acetylneuraminic acid 9-phosphate synthase by a single mutation
Biochem. J.
397
195-201
2006
Homo sapiens
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Hamada, T.; Ito, Y.; Abe, T.; Hayashi, F.; Guentert, P.; Inoue, M.; Kigawa, T.; Terada, T.; Shirouzu, M.; Yoshida, M.; Tanaka, A.; Sugano, S.; Yokoyama, S.; Hirota, H.
Solution structure of the antifreeze-like domain of human sialic acid synthase
Protein Sci.
15
1010-1016
2006
Homo sapiens
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Reaves, M.L.; Lopez, L.C.; Daskalova, S.M.
Replacement of the antifreeze-like domain of human N-acetylneuraminic acid phosphate synthase with the mouse antifreeze-like domain impacts both N-acetylneuraminic acid 9-phosphate synthase and 2-keto-3-deoxy-D-glycero-D-galacto-nonulosonic acid 9-phosphate synthase activities
BMB rep.
41
72-78
2008
Homo sapiens (Q9NR45), Homo sapiens
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Castilho, A.; Pabst, M.; Leonard, R.; Veit, C.; Altmann, F.; Mach, L.; Gloessl, J.; Strasser, R.; Steinkellner, H.
Construction of a functional CMP-sialic acid biosynthesis pathway in Arabidopsis
Plant Physiol.
147
331-339
2008
Homo sapiens
brenda