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Literature summary for 3.4.22.28 extracted from

  • Huang, Y.; Malcolm, B.A.; Vederas, J.C.
    Synthesis and testing of azaglutamine derivatives as inhibitors of hepatitis A virus (HAV) 3C proteinase (1999), Bioorg. Med. Chem., 7, 607-619.
    View publication on PubMed

Inhibitors

Inhibitors Comment Organism Structure
(3S)-[N3-(acetyl-L-leucyl-L-alanyl)-N1-[3'-(N,N-dimethylamino)-3'-oxopropyl]-N1-(methylsulfonyl)]-1,3-diaminobutan-2-one weak competitive Hepatovirus A
(3S)-[N3-(acetyl-L-leucyl-L-alanyl)-N1-[3'-(N,N-dimethylamino)-3'-oxopropyl]-N1-(p-methylphenylsulfonyl)]-1,3-diaminobutan-2-one weak competitive Hepatovirus A
(3S)-[N3-(benzyloxycarbonyl)-N1-[3'-(N,N-dimethylamino)-3'-oxoprolyl]-N1-(methylsulfonyl)]-1,3-diaminobutan-2-one weak competitive Hepatovirus A
(3S)-[N3-(benzyloxycarbonyl)-N1-[3'-(N,N-dimethylamino)-3'-oxopropyl]-N1-(p-methylphenylsulfonyl)]-1,3-diaminobutan-2-one weak competitive, IC50: 0.075 mM Hepatovirus A
3-[N1-(acetyl-L-leucyl-L-alanyl-L-alanyl)-N2-(o-nitrophenyl-sulfenyl)hydrazino]-N,N-(dimethyl)propanamide IC50: 0.1 mM, time-dependent inactivation of the enzyme due to disulfide bond formation with the active site cysteine thiol Hepatovirus A
3-[N1-(bromoacetyl)-N2-(acetyl-L-leucyl-L-alanyl-L-alanyl)hydrazino]-N,N-(dimethyl)propanamide time-dependent irreversible inactivator Hepatovirus A
3-[N1-(chloroacetyl)-N2-(acetyl-L-leucyl-L-alanyl-L-alanyl)hydrazino]1-N,N-(dimethyl)propanamide time-dependent irreversible inactivator Hepatovirus A

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
hepatitis A virus polyprotein + H2O Hepatovirus A the enzyme is essential for cleavage of the initially synthesized viral polyprotein precursor to mature fragents and is therefore required for viral replication in vivo ?
-
?

Organism

Organism UniProt Comment Textmining
coxsackievirus
-
-
-
Hepatovirus A
-
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
hepatitis A virus polyprotein + H2O the enzyme is essential for cleavage of the initially synthesized viral polyprotein precursor to mature fragents and is therefore required for viral replication in vivo Hepatovirus A ?
-
?

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.075
-
weak competitive, IC50: 0.075 mM Hepatovirus A (3S)-[N3-(benzyloxycarbonyl)-N1-[3'-(N,N-dimethylamino)-3'-oxopropyl]-N1-(p-methylphenylsulfonyl)]-1,3-diaminobutan-2-one
0.1
-
IC50: 0.1 mM, time-dependent inactivation of the enzyme due to disulfide bond formation with the active site cysteine thiol Hepatovirus A 3-[N1-(acetyl-L-leucyl-L-alanyl-L-alanyl)-N2-(o-nitrophenyl-sulfenyl)hydrazino]-N,N-(dimethyl)propanamide