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Literature summary for 3.1.1.58 extracted from

  • Chibba, A.; Poloczek, J.; Little, D.J.; Howell, P.L.; Nitz, M.
    Synthesis and evaluation of inhibitors of E. coli PgaB, a polysaccharide de-N-acetylase involved in biofilm formation (2012), Org. Biomol. Chem., 10, 7103-7107.
    View publication on PubMed
Search for more literature for 3.1.1.58

Application

Application Comment Organism
drug development the enzyme is a good target for therapeutic intervention in biofilm related infections Escherichia coli

Inhibitors

Inhibitors Comment Organism Structure
methyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-2-deoxy-2-[[(octanoylsulfanyl)acetyl]amino]-beta-D-lucopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-beta-D-glucopyranoside
-
 Escherichia coli
methyl 2-deoxy-2-(sulfamoylamino)-beta-D-glucopyranoside 9% inhibition at 1 mM Escherichia coli
methyl 2-deoxy-2-[(hydroxyacetyl)(methyl)amino]-beta-D-glucopyranoside 84% inhibition at 1 mM Escherichia coli
methyl 2-deoxy-2-[(hydroxyacetyl)amino]-beta-D-glucopyranoside 8% inhibition at 1 mM Escherichia coli
methyl 2-deoxy-2-[(methylsulfonyl)amino]-beta-D-glucopyranoside 7% inhibition at 1 mM Escherichia coli
methyl 2-deoxy-2-[(sulfanylacetyl)amino]-beta-D-glucopyranoside
-
 Escherichia coli
methyl 2-deoxy-2-[methyl(methylsulfonyl)amino]-beta-D-glucopyranoside 18% inhibition at 1 mM Escherichia coli
methyl 2-deoxy-2-[methyl(sulfamoyl)amino]-beta-D-glucopyranoside 67% inhibition at 1 mM Escherichia coli
methyl 2-deoxy-2-[methyl(sulfanylacetyl)amino]-beta-D-glucopyranoside 48% inhibition at 1 mM Escherichia coli
additional information synthesis and evaluation of a series of enzyme inhibitors, consisting of a metal chelating functional group on a glucosamine scaffold to target the active site metal ion of the enzyme, overview. No or poor inhibitory effect by methyl 2-deoxy-2-(glycylamino)-beta-D-glucopyranoside, methyl 2-deoxy-2-[(hydroxycarbamoyl)amino]-beta-D-glucopyranoside, methyl 2-deoxy-2-[glycyl(methyl)amino]-beta-D-glucopyranoside, and methyl 2-deoxy-2-[(hydroxycarbamoyl)(methyl)amino]-beta-D-glucopyranoside Escherichia coli

Metals/Ions

Metals/Ions Comment Organism Structure
Co2+ activates Escherichia coli
Fe2+ activates Escherichia coli
additional information the enzyme requires an active site metal ion for activity. The enzyme from Escherichia coli has unique metal dependence, showing optimal activity with Fe2+, Ni2+, and Co2+ in contrast to the Zn2+ dependency observed for other N-deacetylases in the CE4 family Escherichia coli
Ni2+ activates Escherichia coli

Natural Substrates/ Products (Substrates)

Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
N-acetylated beta-(1->6)-N-acetylglucosamine polymer + H2O Escherichia coli the enzyme produces partially de-N-acetylated beta-(1->6)-N-acetylglucosamine polymers N-deacetylated beta-(1->6)-N-acetylglucosamine polymer + acetate
-
 ?

Organism

Organism UniProt Comment Textmining
Escherichia coli
-
 gene pgaB
-

Substrates and Products (Substrate)

Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
additional information development of a fluorogenic assay to monitor the enzyme activity in vitro, overview. Monosaccharides are not substrates of the enzyme Escherichia coli ?
-
 ?
N-acetylated beta-(1->6)-N-acetylglucosamine polymer + H2O the enzyme produces partially de-N-acetylated beta-(1->6)-N-acetylglucosamine polymers Escherichia coli N-deacetylated beta-(1->6)-N-acetylglucosamine polymer + acetate
-
 ?

Synonyms

Synonyms Comment Organism
PgaB
-
 Escherichia coli
polysaccharide de-N-acetylase
-
 Escherichia coli

Ki Value [mM]

Ki Value [mM] Ki Value maximum [mM] Inhibitor Comment Organism Structure
0.28
-
 methyl 2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-2-deoxy-2-[[(octanoylsulfanyl)acetyl]amino]-beta-D-lucopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-beta-D-glucopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-beta-D-glucopyranoside pH and temperature not specified in the publication Escherichia coli
0.32
-
 methyl 2-deoxy-2-[(hydroxyacetyl)(methyl)amino]-beta-D-glucopyranoside pH and temperature not specified in the publication Escherichia coli
0.48
-
 methyl 2-deoxy-2-[(sulfanylacetyl)amino]-beta-D-glucopyranoside pH and temperature not specified in the publication Escherichia coli
0.68
-
 methyl 2-deoxy-2-[methyl(sulfamoyl)amino]-beta-D-glucopyranoside pH and temperature not specified in the publication Escherichia coli
0.92
-
 methyl 2-deoxy-2-[methyl(sulfanylacetyl)amino]-beta-D-glucopyranoside pH and temperature not specified in the publication Escherichia coli
5.8
-
 methyl 2-deoxy-2-[methyl(methylsulfonyl)amino]-beta-D-glucopyranoside pH and temperature not specified in the publication Escherichia coli

General Information

General Information Comment Organism
evolution the enzyme belongs to the the carbohydrate esterase family 4, CE4 Escherichia coli
additional information the enzyme has a His-His-Asp metal coordinating triad as well as conserved catalytic residues Escherichia coli
physiological function many medically important biofilm forming bacteria produce similar polysaccharide intercellular adhesins consisting of partially de-N-acetylated beta-(1->6)-N-acetylglucosamine polymers, in Escherichia coli, de-N-acetylation of the beta-(1->6)-N-acetylglucosamine polymer is catalysed by deacetylase PgaB. N-Deacetylation of the polymers is essential for productive partially de-N-acetylated beta-(1->6)-N-acetylglucosamine polymer-dependent biofilm formation Escherichia coli