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(1R,2R)-1-O-(2-acetylamino-2-deoxy-alpha-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate) + H2O
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1-D-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 1-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate) + H2O
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2-acetamido-2-deoxy-alpha-D-glucopyranosyl-(1->6)-phosphatidylinositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
6-(N-butanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + butanoate
6-(N-hexanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + hexanoate
6-(N-isobutanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + isobutanoate
6-(N-pentanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + pentanoate
6-(N-propionyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + propionate
D-GlcNAc-alpha(1->6)-D-myo-inositol-1-octadecyl phosphate + H2O
D-GlcN-alpha(1->6)-D-myo-inositol-1-octadecyl phosphate + acetate
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D-GlcNAc-alpha1-6-D-myo-inositol-1-HPO4-3-sn-1,2-diacylglycerol + H2O
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N,N-diethylethanaminium 1-D-2-[(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)oxy]-myo-inosityl octadecyl phosphate + H2O
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N-acetyl-D-glucosamine-alpha-(1-6)-D-myo-inositol-1-octadecyl phosphate + H2O
D-glucosamine-alpha-(1-6)-D-myo-inositol-1-octadecyl phosphate + acetate
N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
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involved in the formation of the glycosylphosphatidylinositol membrane anchor of the trypanosome variant-surface glycoprotein
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
N-acetyl-D-glucosaminylphosphatidylinositol + H2O + H2O
D-glucosaminylphosphatidylinositol + acetate
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additional information
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
the substrate is prepared from Saccharomyces cerevisiae microsomes. [6-3H]GlcN-PI is converted to [6-3H]GlcNAc-PI using anhydride
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
the substrate is prepared from Saccharomyces cerevisiae microsomes. [6-3H]GlcN-PI is converted to [6-3H]GlcNAc-PI using anhydride
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
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the phosphate, 2'-NHAc and 3'-OH groups of the natural substrate alpha-D-GlcpNAc-PI are critical for recognition by the Trypanosoma brucei GlcNAc-PI de-N-acetylase
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6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
substrate binding analysis by docking with Zn2+ to the enzyme's active site
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6-(N-butanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + butanoate
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very poor substrate
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6-(N-butanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + butanoate
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6-(N-hexanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + hexanoate
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6-(N-hexanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + hexanoate
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6-(N-isobutanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + isobutanoate
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poor substrate
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6-(N-isobutanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + isobutanoate
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6-(N-pentanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + pentanoate
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6-(N-pentanoyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + pentanoate
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6-(N-propionyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + propionate
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6-(N-propionyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O
6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + propionate
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N-acetyl-D-glucosamine-alpha-(1-6)-D-myo-inositol-1-octadecyl phosphate + H2O
D-glucosamine-alpha-(1-6)-D-myo-inositol-1-octadecyl phosphate + acetate
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synthetic substrate
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N-acetyl-D-glucosamine-alpha-(1-6)-D-myo-inositol-1-octadecyl phosphate + H2O
D-glucosamine-alpha-(1-6)-D-myo-inositol-1-octadecyl phosphate + acetate
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synthetic substrate
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
37°C, pH 7.4, 25 mM KCl, 5 mM MgCl2, 5 mM MnCl2, 0.5 mM dithiothreitol, 0.1 mM 1-chloro-3-tosylamido-7-amino-2-heptanone, 1 microg/ml leupeptin
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
37°C
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
30°C, pH 7.4, 50 mM KCl, 10 mM dithiothreitol, 0.1 mM 1-chloro-3-tosylamido-7-amino-2-heptanone, 1 microg/ml leupeptin
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
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N-Acetyl-D-glucosaminylphosphatidylinositol + H2O
D-Glucosaminylphosphatidylinositol + acetate
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analogues lacking the glycerophosphate component are not recognized
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additional information
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the enzyme shows an overall low activity
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additional information
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the enzyme shows an overall low activity
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additional information
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the enzyme shows an overall low activity
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additional information
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no substrate: mannosylated N-acetyl-D-glucosylphosphatidylinositol-derivatives
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additional information
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structural requirements of substrate, enzyme cannot act on analogues containing N-benzoyl-, N-acetyl-D-galactosyl- or N-acetyl-beta-D-glucosyl-groups
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additional information
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structural requirements of substrate, enzyme cannot act on substrate analogues containing N-acetyl-beta-glucosyl-groups or aromatic N-acyl groups
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additional information
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structural requirements of substrate, enzyme can act on analogues containing N-benzoyl-, N-acetyl-D-galactosyl- or N-acetyl-beta-D-glucosyl-groups
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additional information
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structural requirements of substrate, enzyme can act on substrate analogues containing N-acetyl-beta-glucosyl-groups or aromatic N-acyl groups
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additional information
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substrate specificity in decreasing order: N-acetyl-D-glucosylphosphatidylinositol, N-propionylglucosylphosphatidylinositol, N-butyrylglucosylphosphatidylinositol, N-isobutyrylglucosylphosphatidylinositol, N-pentanoylglucosylphosphatidylinositol, N-hexanoylglucosylphosphatidylinositol, no substrate: mannosylated N-acetyl-D-glucosylphosphatidylinositol-derivatives
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additional information
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synthesis of substrate analogues and substrate structure-activity analysis, molecular dynamics simulations, overview. (1R,2R)-1-O-(2-acetylamino-2-deoxy-beta-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate) is neither a substrate nor an inhibitor. No recognition and activity with substrate analogues (1R,2R)-2-[(2-amino-2-deoxy-alpha-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate, (1R,2R)-2-[(2-amino-2-deoxy-beta-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate, (1R,2R)-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate), (1R,2R)-1-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate), N-(1R,2R)-2-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-cyclohexyloctadecane-1-sulphonamide, N-(1R,2R)-2-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-cyclohexyloctadecane-1-sulphonamide, and triethylammonium trans-2-(2-amino-3-hydroxypropoxy)-cyclohexyl n-octadecyl phosphate, as well as with (1R,2R)-2-[(2-acetylamino-2-deoxy-alpha-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate, (1R,2R)-2-[(2-acetamido-2-deoxy-beta-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate, (1R,2R)-1-O-(2-acetylamino-2-deoxy-beta-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate), N-((1R,2R)-2-[(2-acetamido-2-deoxy-beta-D-glucopyranosyl)oxy]cyclohexyl)octadecane-1-sulfonamide, N-((1R,2R)-2-[(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)oxy]cyclohexyl)octadecane-1-sulfonamide, and N,N-diethylethanaminium (1R,2R)-2-(2-acetamido-3-hydroxypropoxy)cyclohexyl octadecyl phosphate. The requirement for the presence of inositol 2-, 3-, 4-, and 5-OH groups for recognition by the enzyme is nuanced and may depend on the conformational flexibility of the substrate analogue. The glucosamine and the phospholipid moieties are essential for binding and, while the D-myo-inositol residue is the preferred aglycone for recognition by the enzyme, the dispensing of it entirely with a cyclohexanediol group is tolerated by the enzyme
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