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Literature summary for 3.4.23.B14 extracted from

  • Luksch, T.; Blum, A.; Klee, N.; Diederich, W.E.; Sotriffer, C.A.; Klebe, G.
    Pyrrolidine derivatives as plasmepsin inhibitors: binding mode analysis assisted by molecular dynamics simulations of a highly flexible protein (2010), ChemMedChem, 5, 443-454.
    View publication on PubMed
Search for more literature for 3.4.23.B14

Inhibitors

Inhibitors Comment Organism Structure
(3S,4S)-pyrrolidine-3,4-diyl bis(3,3-dimethylbutanoate)
-
 Plasmodium falciparum
(3S,4S)-pyrrolidine-3,4-diyl bis(3-methylbutanoate)
-
 Plasmodium falciparum
(3S,4S)-pyrrolidine-3,4-diyl bis(naphthalen-1-ylacetate)
-
 Plasmodium falciparum
(3S,4S)-pyrrolidine-3,4-diyl bis(naphthalen-2-ylacetate)
-
 Plasmodium falciparum
(3S,4S)-pyrrolidine-3,4-diyl bis(phenylacetate)
-
 Plasmodium falciparum
(3S,4S)-pyrrolidine-3,4-diyl dibenzoate
-
 Plasmodium falciparum
(3S,4S)-pyrrolidine-3,4-diyl dicyclohexanecarboxylate
-
 Plasmodium falciparum
additional information pyrrolidine derivatives as plasmepsin inhibitors, binding mode analysis assisted by molecular dynamics simulations, for pyrrolidine-3,4-diester derivatives and a substituted 3,4-diaminopyrrolidine inhibitor by using a crystal structure of inhibitor-bound Plm II, PDB ID 1LEE, and for 3,4-bis(aminomethylene)pyrrolidines, docking studies and modelling, detailed overview. Opening of the S1 and S2’ pockets suggests the design of inhibitors with extended P1 and P2' residues Plasmodium falciparum
N,N'-(3S,4S)-pyrrolidine-3,4-diylbis(N-benzyl-2-phenylacetamide)
-
 Plasmodium falciparum
N-benzyl-2-bromo-N-[[4-([[2-(2,4-dichlorophenyl)ethyl](3-phenylpropyl)amino]methyl)pyrrolidin-3-yl]methyl]-4,5-dimethoxybenzamide
-
 Plasmodium falciparum
N-benzyl-2-bromo-N-[[4-([[2-(2,4-dichlorophenyl)ethyl][2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino]methyl)pyrrolidin-3-yl]methyl]-4,5-dimethoxybenzamide
-
 Plasmodium falciparum
pepstatin A
-
 Plasmodium falciparum

Organism

Organism UniProt Comment Textmining
Plasmodium falciparum
-
-
-

Reaction

Reaction Comment Organism Reaction ID
cleavage of hemoglobin. In the S3 and S2 subsites, the plasmepsin 4 orthologs all prefer hydrophobic amino acid residues, Phe or Ile, but reject charged residues such as Lys or Asp. In S2' and S3' subsites these plasmepsins tolerate both hydrophobic and hydrophilic residues residues D34 and D214 form the catalytic dyad Plasmodium falciparum
a

Synonyms

Synonyms Comment Organism
Plm IV
-
 Plasmodium falciparum

IC50 Value

IC50 Value IC50 Value Maximum Comment Organism Inhibitor Structure
0.00009
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum (3S,4S)-pyrrolidine-3,4-diyl bis(naphthalen-1-ylacetate)
0.00018
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum N-benzyl-2-bromo-N-[[4-([[2-(2,4-dichlorophenyl)ethyl][2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino]methyl)pyrrolidin-3-yl]methyl]-4,5-dimethoxybenzamide
0.00035
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum N-benzyl-2-bromo-N-[[4-([[2-(2,4-dichlorophenyl)ethyl](3-phenylpropyl)amino]methyl)pyrrolidin-3-yl]methyl]-4,5-dimethoxybenzamide
0.0008
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum (3S,4S)-pyrrolidine-3,4-diyl bis(naphthalen-2-ylacetate)
0.0015
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum N,N'-(3S,4S)-pyrrolidine-3,4-diylbis(N-benzyl-2-phenylacetamide)
0.0074
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum (3S,4S)-pyrrolidine-3,4-diyl bis(phenylacetate)
0.0412
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum (3S,4S)-pyrrolidine-3,4-diyl bis(3,3-dimethylbutanoate)
0.0538
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum (3S,4S)-pyrrolidine-3,4-diyl dibenzoate
0.134
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum (3S,4S)-pyrrolidine-3,4-diyl dicyclohexanecarboxylate
0.168
-
 pH not specified in the publication, temperature not speficied in the publication Plasmodium falciparum (3S,4S)-pyrrolidine-3,4-diyl bis(3-methylbutanoate)

General Information

General Information Comment Organism
physiological function the enzyme is involved in host hemoglobin degradation Plasmodium falciparum