Literature summary for 3.4.22.28 extracted from

Lall, M.S.; Ramtohul, Y.K.; James, M.N.; Vederas, J.C.
Serine and threonine beta-lactones: a new class of hepatitis A virus 3C cysteine proteinase inhibitors (2002), J. Org. Chem., 67, 1536-1547.

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Application

Application	Comment	Organism
medicine	the enzyme is essential for viral replication and infectivity and represents a target for the development of antiviral drugs	Hepatovirus A

Inhibitors

Inhibitors	Comment	Organism	Structure
N-(benzyloxycarbonyl)-D-serine-beta-lactone	competitive reversible inhibitor	Hepatovirus A
N-(benzyloxycarbonyl)-L-serine-beta-lactone	irreversible, inactivation of the enzyme occurs by nucleophilic attack of the cysteine thiol Cys172 at the beta-position of the oxetanione ring	Hepatovirus A
N-(methylsulfonyl)-L-serine-beta-lactone	weak time-dependent inhibition	Hepatovirus A
N-(phenethylsulfonyl)-D-serine-beta-lactone	irreversible	Hepatovirus A
N-(phenethylsulfonyl)-L-serine-beta-lactone	reversible	Hepatovirus A
N-(trans-beta-styrenesulfonyl)-D-serine-beta-lactone	reversible	Hepatovirus A
N-(trans-beta-styrenesulfonyl)-L-serine-beta-lactone	reversible	Hepatovirus A

Natural Substrates/ Products (Substrates)

Natural Substrates	Organism	Comment (Nat. Sub.)	Natural Products	Comment (Nat. Pro.)	Rev.	Reac.
picornavirus polyprotein + H2O	Hepatovirus A	the enzyme is essential for viral replication and infectivity	hydrolyzed picornavirus polyprotein	-	?

Organism

Organism	UniProt	Comment	Textmining
Hepatovirus A	-	-	-

Substrates and Products (Substrate)

Substrates	Comment Substrates	Organism	Products	Comment (Products)	Rev.	Reac.
picornavirus polyprotein + H2O	the enzyme is essential for viral replication and infectivity	Hepatovirus A	hydrolyzed picornavirus polyprotein	-	?

Ki Value [mM]

Ki Value [mM]	Ki Value maximum [mM]	Inhibitor	Comment	Organism	Structure
0.0015	-	N-(benzyloxycarbonyl)-D-serine-beta-lactone	pH 7.5, 25°C	Hepatovirus A
0.184	-	N-(benzyloxycarbonyl)-L-serine-beta-lactone	pH 7.5, 25°C	Hepatovirus A

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Release 2023.1 (January 2023)