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Literature summary for 2.3.2.2 extracted from

  • Watanabe, B.; Tabuchi, Y.; Wada, K.; Hiratake, J.
    Synthesis and evaluation of the inhibitory activity of the four stereoisomers of the potent and selective human gamma-glutamyl transpeptidase inhibitor GGsTop (2017), Bioorg. Med. Chem. Lett., 27, 4920-4924 .
    View publication on PubMed
Search for more literature for 2.3.2.2

Inhibitors

Inhibitors Comment Organism Structure
2-amino-4-([3-(carboxymethyl)phenoxy](methoyl)phosphoryl)butanoic acid i.e. GGsTop, a potent and selective, nontoxic, and irreversible inhibitor of human gamma-glutamyl transpeptidase. GGsTop consists of four stereoisomers due to the presence of two stereogenic centers, i.e. the alpha-carbon atom of the glutamate mimic (L/D) and the phosphorus atom (RP/SP), stereoselective synthesis of the 4 isomers. With respect to the configuration of the alpha-carbon atom of the glutamate mimic, the L-isomer is about 8fold more potent than the D-isomer. In contrast, the configuration of the phosphorus atom is critical for GGT inhibitory activity. Based on a molecular modeling approach, the absolute configuration of the phosphorus atom of the active GGsTop isomers is postulated to be SP. The SP-isomers inhibits human GGT, while the RP-isomers are inactive even at concentrations of 0.1 mM Homo sapiens
additional information synthesis and evaluation of the inhibitory activity of the four stereoisomers of inhibitor GGsTop, binding structures of RP-isomer of L-GGsTop and of the SP-isomer of L-GGsTop to GGT active site, modeling, overview Homo sapiens

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
a (5-L-glutamyl)-peptide + an amino acid Homo sapiens
-
 a peptide + a 5-L-glutamyl amino acid
-
 ?

Organism

Organism UniProt Comment Textmining
Homo sapiens P19440
-
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
a (5-L-glutamyl)-peptide + an amino acid
-
 Homo sapiens a peptide + a 5-L-glutamyl amino acid
-
 ?

Synonyms

Synonyms Comment Organism
gamma-glutamyl transpeptidase
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 Homo sapiens
GGT
-
 Homo sapiens

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
additional information
-
 additional information inhibition kinetics, overview Homo sapiens

General Information

General Information Comment Organism
additional information active site structures of human GGT, overview Homo sapiens