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Literature summary extracted from

  • Capes, A.S.; Crossman, A.; Urbaniak, M.D.; Gilbert, S.H.; Ferguson, M.A.; Gilbert, I.H.
    Probing the substrate specificity of Trypanosoma brucei GlcNAc-PI de-N-acetylase with synthetic substrate analogues (2014), Org. Biomol. Chem., 12, 1919-1934.
    View publication on PubMedView publication on EuropePMC

Inhibitors

EC Number Inhibitors Comment Organism Structure
3.5.1.89 (1R,2R)-1-O-(2-acetylamino-2-deoxy-alpha-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate) competitive Trypanosoma brucei
3.5.1.89 (1R,2R)-1-O-(2-acetylamino-2-deoxy-beta-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate)
-
 Trypanosoma brucei
3.5.1.89 (1R,2R)-1-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate)
-
 Trypanosoma brucei
3.5.1.89 (1R,2R)-1-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate)
-
 Trypanosoma brucei
3.5.1.89 (1R,2R)-2-((2-deoxy-2-[(hydroxycarbamoyl)amino]-beta-D-glucopyranosyl)oxy)cyclohexyl octadecyl phosphate
-
 Trypanosoma brucei
3.5.1.89 (1R,2R)-2-[(2-acetamido-2-deoxy-beta-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate
-
 Trypanosoma brucei
3.5.1.89 (1R,2R)-2-[(2-acetylamino-2-deoxy-alpha-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate
-
 Trypanosoma brucei
3.5.1.89 (1R,2R)-2-[(2-amino-2-deoxy-alpha-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate
-
 Trypanosoma brucei
3.5.1.89 (1R,2R)-2-[(2-amino-2-deoxy-beta-D-glucopyranosyl)oxy]cyclohexyl octadecyl phosphate
-
 Trypanosoma brucei
3.5.1.89 additional information (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 Trypanosoma brucei
3.5.1.89 N,N-diethylethanaminium (1R,2R)-2-(2-acetamido-3-hydroxypropoxy)cyclohexyl octadecyl phosphate
-
 Trypanosoma brucei
3.5.1.89 N,N-diethylethanaminium 1-D-2-[(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)oxy]-myo-inosityl octadecyl phosphate
-
 Trypanosoma brucei
3.5.1.89 N-((1R,2R)-2-[(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)oxy]cyclohexyl)octadecane-1-sulfonamide
-
 Trypanosoma brucei
3.5.1.89 N-((1R,2R)-2-[(2-acetamido-2-deoxy-beta-D-glucopyranosyl)oxy]cyclohexyl)octadecane-1-sulfonamide
-
 Trypanosoma brucei
3.5.1.89 N-(1R,2R)-2-O-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-cyclohexyloctadecane-1-sulphonamide
-
 Trypanosoma brucei
3.5.1.89 N-(1R,2R)-2-O-(2-amino-2-deoxy-beta-D-glucopyranosyl)-cyclohexyloctadecane-1-sulphonamide
-
 Trypanosoma brucei
3.5.1.89 triethylammonium trans-2-(2-amino-3-hydroxypropoxy)-cyclohexyl n-octadecyl phosphate
-
 Trypanosoma brucei

Metals/Ions

EC Number Metals/Ions Comment Organism Structure
3.5.1.89 Mn2+ activates Trypanosoma brucei
3.5.1.89 Zn2+ a zinc-dependent metalloenzyme Trypanosoma brucei

Natural Substrates/ Products (Substrates)

EC Number Natural Substrates Organism Comment (Nat. Sub.) Natural Products Comment (Nat. Pro.) Rev. Reac.
3.5.1.89 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O Trypanosoma brucei 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 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
-
 ?

Organism

EC Number Organism UniProt Comment Textmining
3.5.1.89 Trypanosoma brucei
-
-
-

Substrates and Products (Substrate)

EC Number Substrates Comment Substrates Organism Products Comment (Products) Rev. Reac.
3.5.1.89 (1R,2R)-1-O-(2-acetylamino-2-deoxy-alpha-D-glucopyranosyl)-cyclohexanediol 2-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate) + H2O
-
 Trypanosoma brucei ?
-
 ?
3.5.1.89 1-D-(2-amino-2-deoxy-alpha-D-glucopyranosyl)-myo-inositol 1-(1,2-di-O-hexadecanoyl-sn-glycerol 3-phosphate) + H2O
-
 Trypanosoma brucei ?
-
 ?
3.5.1.89 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O 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 Trypanosoma brucei 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate
-
 ?
3.5.1.89 additional information 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 Trypanosoma brucei ?
-
 ?
3.5.1.89 N,N-diethylethanaminium 1-D-2-[(2-acetamido-2-deoxy-alpha-D-glucopyranosyl)oxy]-myo-inosityl octadecyl phosphate + H2O
-
 Trypanosoma brucei ?
-
 ?

Synonyms

EC Number Synonyms Comment Organism
3.5.1.89 GlcNAc-PI de-N-acetylase
-
 Trypanosoma brucei

Temperature Optimum [°C]

EC Number Temperature Optimum [°C] Temperature Optimum Maximum [°C] Comment Organism
3.5.1.89 37
-
 assay at Trypanosoma brucei

pH Optimum

EC Number pH Optimum Minimum pH Optimum Maximum Comment Organism
3.5.1.89 8
-
 assay at Trypanosoma brucei

General Information

EC Number General Information Comment Organism
3.5.1.89 metabolism the enzyme is responsible for the second step in the glycosylphosphatidylinositol biosynthetic pathway of Trypanosoma brucei, which is a prerequisite for all subsequent steps in the pathway Trypanosoma brucei