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Literature summary extracted from

  • Grembecka, J.; Mucha, A.; Cierpicki, T.; Kafarski, P.
    The most potent organophosphorus inhibitors of leucine aminopeptidase. Structure-based design, chemistry, and activity (2003), J. Med. Chem., 46, 2641-2655.
    View publication on PubMed

Application

EC Number Application Comment Organism
3.4.11.1 medicine enzyme is a target for inhibitor design Sus scrofa
3.4.11.2 medicine enzyme is a target for inhibitor design Sus scrofa

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.4.11.1 2-[[(1-amino-3-methylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid (R)-isomer and 1:1 ratio of the 2 diastereomers Sus scrofa
3.4.11.1 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-(4-hydroxyphenyl)propionic acid
-
 Sus scrofa
3.4.11.1 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-phenylpropionic acid
-
 Sus scrofa
3.4.11.1 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid
-
 Sus scrofa
3.4.11.1 3-[(1-amino-3-methylbutyl)hydroxyphosphinyl]-propionic acid
-
 Sus scrofa
3.4.11.1 additional information computational inhibitor design Sus scrofa
3.4.11.1 N-[(1-hydroxy-3-methylbutyl)oxyphosphinyl]glycine dilithium salt
-
 Sus scrofa
3.4.11.2 2-[[(1-amino-3-methylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid (R)-isomer and 1:1 ratio of the 2 diastereomers Sus scrofa
3.4.11.2 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-(4-hydroxyphenyl)propionic acid
-
 Sus scrofa
3.4.11.2 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-phenylpropionic acid
-
 Sus scrofa
3.4.11.2 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid
-
 Sus scrofa
3.4.11.2 3-[(1-amino-3-methylbutyl)hydroxyphosphinyl]-propionic acid
-
 Sus scrofa
3.4.11.2 additional information computational inhibitor design, inhibition mechanism, structural requirements of phosphinate inhibitors for binding and inhibition, overview Sus scrofa
3.4.11.2 N-[(1-hydroxy-3-methylbutyl)oxyphosphinyl]glycine dilithium salt
-
 Sus scrofa

Localization

EC Number Localization Comment Organism GeneOntology No. Textmining
3.4.11.1 cytosol
-
 Sus scrofa 5829
-

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
3.4.11.1 Zn2+ zinc-containing metallopeptidase Sus scrofa

Organism

EC Number Organism UniProt Comment Textmining
3.4.11.1 Sus scrofa
-
-
-
3.4.11.2 Sus scrofa
-
-
-

Reaction

EC Number Reaction Comment Organism Reaction ID
3.4.11.1 release of an N-terminal amino acid, Xaa-/-Yaa-, in which Xaa is preferably Leu, but may be other amino acids including Pro although not Arg or Lys, and Yaa may be Pro. Amino acid amides and methyl esters are also readily hydrolysed, but rates on arylamides are exceedingly low exopeptidase Sus scrofa
a

Source Tissue

EC Number Source Tissue Comment Organism Textmining
3.4.11.1 commercial preparation
-
 Sus scrofa
-
3.4.11.1 kidney
-
 Sus scrofa
-
3.4.11.2 commercial preparation
-
 Sus scrofa
-
3.4.11.2 kidney
-
 Sus scrofa
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.4.11.1 L-Leu-4-nitroanilide + H2O
-
 Sus scrofa L-Leu + 4-nitroaniline
-
 ?
3.4.11.2 L-Leu-4-nitroanilide + H2O
-
 Sus scrofa L-Leu + 4-nitroaniline
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.4.11.1 LAP
-
 Sus scrofa
3.4.11.1 leucine aminopeptidase
-
 Sus scrofa
3.4.11.2 aminopeptidase N
-
 Sus scrofa
3.4.11.2 APN
-
 Sus scrofa

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.4.11.1 25
-
 assay at Sus scrofa

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.4.11.1 8.4
-
 assay at Sus scrofa

Ki Value [mM]

EC Number Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
3.4.11.1 0.000065
-
 2-[[(1-amino-3-methylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid pH 8.4, 25°C, 1:1 ratio of the 2 diastereomers Sus scrofa
3.4.11.1 0.000066
-
 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-phenylpropionic acid pH 8.4, 25°C Sus scrofa
3.4.11.1 0.000067
-
 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-(4-hydroxyphenyl)propionic acid pH 8.4, 25°C Sus scrofa
3.4.11.1 0.000074
-
 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid pH 8.4, 25°C Sus scrofa
3.4.11.1 0.00011
-
 2-[[(1-amino-3-methylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid pH 8.4, 25°C, (R)-isomer Sus scrofa
3.4.11.1 0.00033
-
 3-[(1-amino-3-methylbutyl)hydroxyphosphinyl]-propionic acid pH 8.4, 25°C Sus scrofa
3.4.11.1 0.00488
-
 N-[(1-hydroxy-3-methylbutyl)oxyphosphinyl]glycine dilithium salt pH 8.4, 25°C Sus scrofa
3.4.11.2 0.000036
-
 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-(4-hydroxyphenyl)propionic acid pH 8.4, 25°C Sus scrofa
3.4.11.2 0.000276
-
 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-3-phenylpropionic acid pH 8.4, 25°C Sus scrofa
3.4.11.2 0.001
-
 2-[[(1-amino-4-phenylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid pH 8.4, 25°C Sus scrofa
3.4.11.2 0.00102
-
 2-[[(1-amino-3-methylbutyl)hydroxyphosphinyl]methyl]-4-methylpentanoic acid pH 8.4, 25°C, 1:1 ratio of the 2 diastereomers Sus scrofa
3.4.11.2 0.00142
-
 3-[(1-amino-3-methylbutyl)hydroxyphosphinyl]-propionic acid pH 8.4, 25°C Sus scrofa