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Literature summary extracted from

  • Stanley, M.; Mayr, J.; Huber, W.; Vlasak, R.; Streicher, H.
    Synthesis and inhibitory activity of sialic acid derivatives targeted at viral sialate-O-acetylesterases (2011), Eur. J. Med. Chem., 46, 2852-2860.
    View publication on PubMed

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.1.1.53 3,4-dichloroisocoumarin
-
bovine coronavirus
3.1.1.53 3,4-dichloroisocoumarin
-
influenza C virus
3.1.1.53 3,4-dichloroisocoumarin
-
Murine hepatitis virus
3.1.1.53 3,4-dichloroisocoumarin
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 ammonium (allyl 5-acetamido-3,5-dideoxy-4-O-methyl-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
Murine hepatitis virus
3.1.1.53 ammonium (allyl 5-acetamido-3,5-dideoxy-4-O-methyl-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 ammonium (allyl 5-acetamido-9-O-methyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
bovine coronavirus
3.1.1.53 ammonium (allyl 5-acetamido-9-O-methyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
influenza C virus
3.1.1.53 diammonium (allyl 5-acetamido-3,5-dideoxy-4-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
Murine hepatitis virus
3.1.1.53 diammonium (allyl 5-acetamido-3,5-dideoxy-4-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 diammonium (allyl 5-acetamido-3,5-dideoxy-9-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
bovine coronavirus
3.1.1.53 diammonium (allyl 5-acetamido-3,5-dideoxy-9-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate)
-
influenza C virus
3.1.1.53 additional information synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-O-acetylesterase from Influenza C virus. No inhibition of Bovine coronavirus by ammonium (allyl 5-acetamido-3,5-dideoxy-4-O-methyl-D-glycero-alpha-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-4-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate) bovine coronavirus
3.1.1.53 additional information synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-Oacetylesterase from Influenza C virus. No inhibition of Influenza C virus by ammonium (allyl 5-acetamido-3,5-dideoxy-4-O-methyl-D-glycero-a-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-4-O-(P-methylphosphonyl)-D-glycero-a-d-galacto-2-nonulopyranosidonate) influenza C virus
3.1.1.53 additional information synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-O-acetylesterase from Influenza C virus. No inhibition of Mouse hepatitis virus strain S by ammonium (allyl 5-acetamido-9-O-methyl-3,5-dideoxy-D-glycero-alpha-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-9-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate) Murine hepatitis virus
3.1.1.53 additional information synthesis and evaluation of a series of sialosides modified at the 4- and 9-hydroxy group for inhibition of the viral haemagglutinin-esterase activity from various Orthomyxoviruses and Coronaviruses, overview. While no inhibition of the sialate-4-O-acetylesterases from Mouse hepatitis virus strain S or Sialodacryoadenitis virus is found, a 9-O-methyl derivative displays inhibitory activity against recombinant sialate-9-O-acetylesterase from Influenza C virus. No inhibition of Rat sialoadacryoadenitis coronavirus by ammonium (allyl 5-acetamido-9-O-methyl-3,5-dideoxy-dglycero-alpha-D-galacto-2-nonulopyranosidonate) and diammonium (allyl 5-acetamido-3,5-dideoxy-9-O-(P-methylphosphonyl)-D-glycero-alpha-D-galacto-2-nonulopyranosidonate) Rat sialodacryoadenitis coronavirus

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.1.1.53 additional information bovine coronavirus the enzyme of Bovine coronavirus exhibits sialate-9-O-acetylesterase specificity ?
-
?
3.1.1.53 additional information influenza C virus the enzyme of Influenza C virus exhibits sialate-9-O-acetylesterase specificity ?
-
?
3.1.1.53 additional information Murine hepatitis virus the enzyme of Influenzy C virus exhibits sialate-4-O-acetylesterase specificity ?
-
?
3.1.1.53 additional information Rat sialodacryoadenitis coronavirus the enzyme of Rat sialoadacryoadenitis coronavirus exhibits sialate-4-O-acetylesterase specificity ?
-
?

Organism

EC Number Organism UniProt Comment Textmining
3.1.1.53 bovine coronavirus
-
BcoV
-
3.1.1.53 influenza C virus
-
-
-
3.1.1.53 Murine hepatitis virus
-
-
-
3.1.1.53 Rat sialodacryoadenitis coronavirus
-
SDAV
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.1.1.53 4-nitrophenyl acetate + H2O
-
influenza C virus 4-nitrophenol + acetate
-
?
3.1.1.53 4-nitrophenyl acetate + H2O
-
Murine hepatitis virus 4-nitrophenol + acetate
-
?
3.1.1.53 4-nitrophenyl acetate + H2O
-
bovine coronavirus 4-nitrophenol + acetate
-
?
3.1.1.53 4-nitrophenyl acetate + H2O
-
Rat sialodacryoadenitis coronavirus 4-nitrophenol + acetate
-
?
3.1.1.53 additional information the enzyme of Bovine coronavirus exhibits sialate-9-O-acetylesterase specificity bovine coronavirus ?
-
?
3.1.1.53 additional information the enzyme of Influenza C virus exhibits sialate-9-O-acetylesterase specificity influenza C virus ?
-
?
3.1.1.53 additional information the enzyme of Influenzy C virus exhibits sialate-4-O-acetylesterase specificity Murine hepatitis virus ?
-
?
3.1.1.53 additional information the enzyme of Rat sialoadacryoadenitis coronavirus exhibits sialate-4-O-acetylesterase specificity Rat sialodacryoadenitis coronavirus ?
-
?

Synonyms

EC Number Synonyms Comment Organism
3.1.1.53 4-SOAE
-
influenza C virus
3.1.1.53 4-SOAE
-
Murine hepatitis virus
3.1.1.53 4-SOAE
-
bovine coronavirus
3.1.1.53 4-SOAE
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 9-SOAE
-
influenza C virus
3.1.1.53 9-SOAE
-
Murine hepatitis virus
3.1.1.53 9-SOAE
-
bovine coronavirus
3.1.1.53 9-SOAE
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 sialate-4-O-acetylesterase
-
influenza C virus
3.1.1.53 sialate-4-O-acetylesterase
-
Murine hepatitis virus
3.1.1.53 sialate-4-O-acetylesterase
-
bovine coronavirus
3.1.1.53 sialate-4-O-acetylesterase
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 sialate-9-O-acetylesterase
-
influenza C virus
3.1.1.53 sialate-9-O-acetylesterase
-
Murine hepatitis virus
3.1.1.53 sialate-9-O-acetylesterase
-
bovine coronavirus
3.1.1.53 sialate-9-O-acetylesterase
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 sialate-O-acetylesterase
-
influenza C virus
3.1.1.53 sialate-O-acetylesterase
-
Murine hepatitis virus
3.1.1.53 sialate-O-acetylesterase
-
bovine coronavirus
3.1.1.53 sialate-O-acetylesterase
-
Rat sialodacryoadenitis coronavirus
3.1.1.53 SOAE
-
influenza C virus
3.1.1.53 SOAE
-
Murine hepatitis virus
3.1.1.53 SOAE
-
bovine coronavirus
3.1.1.53 SOAE
-
Rat sialodacryoadenitis coronavirus

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.1.1.53 22
-
assay at room temperature influenza C virus
3.1.1.53 22
-
assay at room temperature Murine hepatitis virus
3.1.1.53 22
-
assay at room temperature bovine coronavirus
3.1.1.53 22
-
assay at room temperature Rat sialodacryoadenitis coronavirus

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.1.1.53 7.4
-
assay at influenza C virus
3.1.1.53 7.4
-
assay at Murine hepatitis virus
3.1.1.53 7.4
-
assay at bovine coronavirus
3.1.1.53 7.4
-
assay at Rat sialodacryoadenitis coronavirus

General Information

EC Number General Information Comment Organism
3.1.1.53 physiological function besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Bovine coronavirus exhibits sialate-9-O-acetylesterase specificity bovine coronavirus
3.1.1.53 physiological function besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Influenza C virus exhibits sialate-9-O-acetylesterase specificity influenza C virus
3.1.1.53 physiological function besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Mouse hepatitis virus strain S exhibits sialate-4-O-acetylesterase specificity Murine hepatitis virus
3.1.1.53 physiological function besides sialidases, the haemagglutinin-esterases of Influenza C virus, Isavirus, Betacoronaviruses and Toroviruses represent another class of receptor-destroying enzymes, RDEs. They are sialate-O-acetylesterases, SOAE, hydrolysing O-acetyl esters of O-acetylated sialic acid derivatives as sialate-4-O-acetylesterases, 4-SOAE, and sialate-9-O-acetylesterases, 9-SOAE. The enzyme of Rat sialoadacryoadenitis coronavirus exhibits sialate-4-O-acetylesterase specificity Rat sialodacryoadenitis coronavirus