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Literature summary for 3.1.1.53 extracted from

  • Mayr, J.; Haselhorst, T.; Langereis, M.A.; Dyason, J.C.; Huber, W.; Frey, B.; Vlasak, R.; de Groot, R.J.; von Itzstein, M.
    Influenza C virus and bovine coronavirus esterase reveal a similar catalytic mechanism: new insights for drug discovery (2008), Glycoconj. J., 25, 393-399.
    View publication on PubMed
Search for more literature for 3.1.1.53

Application

Application Comment Organism
drug development drug design, two essential pharmacophoric groups of ligand: 9-O-acetyl group and C-1 carboxylate group, anti-virus infection bovine coronavirus
drug development drug design, two essential pharmacophoric groups of ligand: 9-O-acetyl group and C-1 carboxylate group, anti-virus infection influenza C virus

Crystallization (Commentary)

Crystallization (Comment) Organism
molecular modelling using PDB: 1FLC, and alpha-methyl or beta-methyl glycosides of 9-acetamido-9-deoxy-N-acetylneuraminic acid or N-acetyl-9-O-acetyl-2,6-alpha-S-glucosyl-neuraminic acid alpha-methylglycoside as substrates, no interaction between aglycon moiety and the enzyme or its active site, catalytic triad: Ser57, His355, Asp352, catalysis involves conformational change of Ser57 side chain in order to enable 9-O-acetyl-binding and position for nucleophilic attack on 9-O-acetate carbonyl carbon, beta-anomer substrate lacks bi-dendate interaction between C-1 carboxylate group and Asp352 and is no suitable substrate influenza C virus

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
additional information bovine coronavirus alpha-anomer specificity ?
-
 ?
additional information influenza C virus alpha-anomer specificity ?
-
 ?
additional information influenza C virus Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling ?
-
 ?
additional information influenza C virus Johannesburg alpha-anomer specificity ?
-
 ?
additional information influenza C virus Johannesburg Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling ?
-
 ?
additional information bovine coronavirus BcoV alpha-anomer specificity ?
-
 ?

Organism

Organism UniProt Comment Textmining
bovine coronavirus
-
 BcoV
-
bovine coronavirus BcoV
-
 BcoV
-
influenza C virus P07975 INF-C
-
influenza C virus Johannesburg P07975 INF-C
-

Purification (Commentary)

Purification (Comment) Organism
from baculovirus infected insect Sf9 cells as GFP-fusion protein by ultracentrifugation, ion-exchange chromatography on Q-Sepharose FF column and dialysis influenza C virus

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
methyl 6-O-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + H2O methyl N-acetylneuraminide, 25°C, 60 min, pH 7 bovine coronavirus methyl 6-O-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate NMR-based enzyme assay ?
methyl 6-S-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-6-thio-alpha-D-glucoside + H2O thio-linked N-acetylneuraminosylglucoside, 25°C, 60 min, pH 7 bovine coronavirus methyl 6-S-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate NMR-based enzyme assay ?
methyl 6-S-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-6-thio-alpha-D-glucoside + H2O thio-linked N-acetylneuraminosylglucoside, 25°C, 60 min, pH 7 influenza C virus methyl 6-S-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate NMR-based enzyme assay ?
methyl 6-S-(N-acetyl-9-O-acetyl-alpha-D-neuramin-2-yl)-6-thio-alpha-D-glucoside + H2O thio-linked N-acetylneuraminosylglucoside, 25°C, 60 min, pH 7 bovine coronavirus BcoV methyl 6-S-(N-acetyl-alpha-D-neuramin-2-yl)-alpha-D-glucoside + acetate NMR-based enzyme assay ?
additional information alpha-anomer specificity bovine coronavirus ?
-
 ?
additional information alpha-anomer specificity influenza C virus ?
-
 ?
additional information Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling influenza C virus ?
-
 ?
additional information enzyme activity independent of chemical nature of aglycon moiety influenza C virus ?
-
 ?
additional information specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25°C, pH 7) bovine coronavirus ?
-
 ?
additional information specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25°C, pH 7) influenza C virus ?
-
 ?
additional information substrate specificity towards aglycon moiety bovine coronavirus ?
-
 ?
additional information alpha-anomer specificity influenza C virus Johannesburg ?
-
 ?
additional information Ser57 is essential for substrate binding and orientation and catalytic activity, NMR-analyses and molecular modelling influenza C virus Johannesburg ?
-
 ?
additional information enzyme activity independent of chemical nature of aglycon moiety influenza C virus Johannesburg ?
-
 ?
additional information specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25°C, pH 7) influenza C virus Johannesburg ?
-
 ?
additional information alpha-anomer specificity bovine coronavirus BcoV ?
-
 ?
additional information specific for alpha-anomer of N-acetyl-9-O-acetyl-neuraminic acid, N-acetyl-9-O-acetyl-neuraminic acid beta-methylglycoside is no substrate (60 min, 25°C, pH 7) bovine coronavirus BcoV ?
-
 ?
additional information substrate specificity towards aglycon moiety bovine coronavirus BcoV ?
-
 ?
N-acetyl-9-O-acetyl-neuraminic acid + H2O 25°C, 60 min, pH 7, slow activity due to alpha: beta anomeric ratio of about 5: 95 bovine coronavirus N-acetylneuraminic acid + acetate NMR-based enzyme assay ?
N-acetyl-9-O-acetyl-neuraminic acid + H2O 25°C, 60 min, pH 7, slow activity due to alpha: beta anomeric ratio of about 5:95 influenza C virus N-acetylneuraminic acid + acetate NMR-based enzyme assay ?
N-acetyl-9-O-acetyl-neuraminic acid alpha-methylglycoside + H2O methyl N-acetylneuraminide, 25°C, 60 min, pH 7 influenza C virus N-acetylneuraminic acid alpha-methylglycoside + acetate NMR-based enzyme assay ?
p-nitrophenyl acetate + H2O
-
 bovine coronavirus p-nitrophenol + acetate
-
 ?
p-nitrophenyl acetate + H2O
-
 influenza C virus p-nitrophenol + acetate
-
 ?
p-nitrophenyl acetate + H2O
-
 influenza C virus Johannesburg p-nitrophenol + acetate
-
 ?
p-nitrophenyl acetate + H2O
-
 bovine coronavirus BcoV p-nitrophenol + acetate
-
 ?

Synonyms

Synonyms Comment Organism
haemagglutinin esterase
-
 bovine coronavirus
haemagglutinin esterase fusion
-
 influenza C virus
HE
-
 bovine coronavirus
HEF
-
 influenza C virus
INF-C esterase
-
 influenza C virus

Turnover Number [1/s]

Turnover Number Minimum [1/s] Turnover Number Maximum [1/s] Substrate Comment Organism Structure
additional information
-
 additional information methyl-linked N-acetyl-neuraminide (N-acetyl-9-O-acetyl-neuraminic acid alpha-methylglycoside) and thio-linked N-acetylneuraminosylglucoside (N-acetyl-9-O-acetyl-2,6-alpha-S-glucosyl-neuraminic acid alpha-methylglycoside) hydrolysed at similar rates influenza C virus
additional information
-
 additional information methyl-linked N-acetyl-neuraminide (N-acetyl-9-O-acetyl-neuraminic acid alpha-methylglycoside) hydrolysed at higher rate than thio-linked N-acetylneuraminosylglucoside (N-acetyl-9-O-acetyl-2,6-alpha-S-glucosyl-neuraminic acid alpha-methylglycoside) bovine coronavirus