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Basic Ligand Information
Roles as Enzyme Ligand
Enzyme Kinetic Parameters
References & Links
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Ligand N-acetyl-D-glucosaminylphosphatidylinositol

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Basic Ligand Information

Molecular Structure

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Molecular Formula

BRENDA Name

InChIKey

C₂₅H₄₂NO₁₈PR₂

N-acetyl-D-glucosaminylphosphatidylinositol

Synonyms:

6(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol, 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol, D-GlcNAc-alpha1-6-D-myo-inositol-1-HPO4-3-sn-1,2-diacylglycerol, N-acetyl-D-glucosaminyl-phosphatidylinositol, N-acetyl-D-glucosylphosphatidylinositol

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.89

6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O = 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate

734251, 756513, 756746, 734824

3.5.1.89

N-Acetyl-D-glucosaminylphosphatidylinositol + H2O = ?

288963

3.5.1.89

N-Acetyl-D-glucosaminylphosphatidylinositol + H2O = D-Glucosaminylphosphatidylinositol + acetate

719943

3.5.1.89

3 entries

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.198

UDP-N-acetyl-alpha-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol

2.4.1.198

UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol

2.4.1.198

UDP-N-acetyl-D-glucosamine + phosphatidylinositol = UDP + N-acetyl-D-glucosaminyl-phosphatidylinositol

2.4.1.198

3 entries

Substrate in Enzyme-catalyzed Reactions (5 results)

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EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

3.5.1.89

6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + H2O = 6-(alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol + acetate

649652, 734251, 756513, 756746, 734824

3.5.1.89

D-GlcNAc-alpha1-6-D-myo-inositol-1-HPO4-3-sn-1,2-diacylglycerol + H2O = ?

684885

3.5.1.89

N-acetyl-D-glucosaminylphosphatidylinositol + H2O + H2O = D-glucosaminylphosphatidylinositol + acetate

719266

3.5.1.89

N-Acetyl-D-glucosaminylphosphatidylinositol + H2O = ?

288963

3.5.1.89

N-Acetyl-D-glucosaminylphosphatidylinositol + H2O = D-Glucosaminylphosphatidylinositol + acetate

663871, 684885, 665179, 719943, 288963, 288964, 665630, 665504

3.5.1.89

5 entries

Product in Enzyme-catalyzed Reactions (3 results)

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Show Product (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.198

UDP-N-acetyl-alpha-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol

2.4.1.198

UDP-N-acetyl-D-glucosamine + 1-phosphatidyl-1D-myo-inositol = UDP + 6-(N-acetyl-alpha-D-glucosaminyl)-1-phosphatidyl-1D-myo-inositol

2.4.1.198

UDP-N-acetyl-D-glucosamine + phosphatidylinositol = UDP + N-acetyl-D-glucosaminyl-phosphatidylinositol

638133, 638130, 288963, 0, 638129, 638128, 638131, 638132, 638134, 638135

2.4.1.198

3 entries

Enzyme Kinetic Parameters

K_M Value (11 results)

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Show KM Value (11 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

3.5.1.89

0.00015

288964

3.5.1.89

0.00137

pH 5.5, 37Â°C, recombinant mutant H140A cytoplasmic catalytic domain, metal added

734251

3.5.1.89

0.0016

pH 5.5, 37Â°C, recombinant mutant H140A cytoplasmic catalytic domain, no metal added

734251

3.5.1.89

0.00182

pH 5.5, 37Â°C, recombinant mutant D46A cytoplasmic catalytic domain, no metal added

734251

3.5.1.89

0.00195

pH 5.5, 37Â°C, recombinant mutant D46A cytoplasmic catalytic domain, metal added

734251

3.5.1.89

0.00195

pH 5.5, 37Â°C, recombinant wild-type cytoplasmic catalytic domain, no metal added

734251

3.5.1.89

0.00195

in the absence of metal ions, in 50 mM acetate buffer at pH 5.5 and 37Â°C

719943

3.5.1.89

0.00199

pH 5.5, 37Â°C, recombinant mutant H43A cytoplasmic catalytic domain, no metal added

734251

3.5.1.89

0.00205

in the presence of 5 mM Mn2+, in 50 mM acetate buffer at pH 5.5 and 37Â°C

719943

3.5.1.89

0.00209

pH 5.5, 37Â°C, recombinant wild-type cytoplasmic catalytic domain, metal added

734251

3.5.1.89

0.00263

pH 5.5, 37Â°C, recombinant mutant H43A cytoplasmic catalytic domain, metal added

734251

3.5.1.89

11 entries

References & Links

Literature References (22)

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Show Reference (22 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

288963

2525555

Biosynthesis of the glycosyl phosphatidylinositol membrane anchor of the trypanosome variant surface glycoprotein. Origin of the non-acetylated glucosamine

1989

Doering, T.L.; Masterson, W.J.; Englund, P.T.; Hart, G.W.

J. Biol. Chem.

264

11168-11173

288964

8206949

Partial purification and characterization of the N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase of glycosylphosphatidylinositol anchor biosynthesis in African trypanosomes

1994

Milne, K.G.; Field, R.A.; Masterson, W.J.; Cooaz, S.; Brimacombe, J.S.; Ferguson, M.A.J.

J. Biol. Chem.

269

16403-16408

638128

1325903

Inhibition of the GlcNAc transferase of the glycosylphosphatidylinositol anchor biosynthesis in African trypanosomes

1992

Milne, K.G.; Ferguson, M.A.J.; Masterson, W.J.

Eur. J. Biochem.

208

309-314

638129

8389477

Specific defect in N-acetylglucosamine incorporation in the biosynthesis of the glycosylphosphatidylinositol anchor in cloned cell lines from patients with paroxysmal nocturnal hemoglobinuria

1993

Hillmen, P.; Bessler, M.; Mason, P.J.; Watkins, W.M.; Luzzatto, L.

Proc. Natl. Acad. Sci. USA

5272-5276

638130

Activity of phosphatidylinositol/UDP-GlcNAc:GlcNAc transferase in midgut tissue of Bombyx mori

2003

Takano, D.; Kishimoto, T.; Hayakawa, T.; Mitsui, T.; Hori, H.

Niigata Daigaku Nogakubu Kenkyu Hokoku

123-131

638131

9463366

The first step of glycosylphosphatidylinositol biosynthesis is mediated by a complex of PIG-A, PIG-H, PIG-C and GPI1

1998

Watanabe, R.; Inoue, N.; Westfall, B.; Taron, C.H.; Orlean, P.; Takeda, J.; Kinoshita, T.

EMBO J.

877-885

638132

10373468

GPI1 stabilizes an enzyme essential in the first step of glycosylphosphatidylinositol biosynthesis

1999

Hong, Y.; Oshihi, K.; Watanabe, R.; Endo, Y.; Maeda, Y.; Kinoshita, T.

J. Biol. Chem.

274

18582-18588

638133

Segregation of glycosylphosphatidylinositol biosynthetic reactions in a subcompartment of the endoplasmic reticulum

1999

Vidugiriene, J.; Sharma, D.K.; Smith, T.K.; Baumann, N.A.; Menon, A.K.

J. Biol. Chem.

274

15202-15212

638134

10944123

Initial enzyme for glycosylphosphatidylinositol biosynthesis requires PIG-P and is regulated by DPM2

2000

Watanabe, R.; Murakami, Y.; Marmor, M.; Inoue, N.; Maeda, Y.; Hino, J.; Kangawa, K.; Julius, M.; Kinoshita, T.

EMBO J.

4402-4411

638135

Photoaffinity labelling with P3-(4-azidoanilido)uridine 5'-triphosphate identifies Gpi3p as the UDP-GlcNAc-binding subunit of the enzyme that catalyses formation of GlcNAc-phosphatidylinositol, the first glycolipid intermediate in glycosylphosphatidylinositol synthesis

2000

Kostova, Z.; Rancour, D.M.; Menon, A.K.; Orlean, P.

Biochem. J.

350

815-822

649652

9359849

Substrate specificity of the N-acetylglucosaminyl-phosphatidylinositol de-N-acetylase of glycosylphosphatidylinositol membrane anchor biosynthesis in African trypanosomes and human cells

1997

Sharma, D.K.; Smith, T.K.; Crossman, A.; Brimacombe, J.S.; Ferguson, M.A.J.

Biochem. J.

328

171-177

663871

15781246

Raft-like membrane domains contain enzymatic activities involved in the synthesis of mammalian glycosylphosphatidylinositol anchor intermediates

2005

Pielsticker, L.K.; Mann, K.J.; Lin, W.L.; Sevlever, D.

Biochem. Biophys. Res. Commun.

330

163-171

665179

16299336

Reduction of cell surface glycosylphosphatidylinositol conjugates in Entamoeba histolytica by antisense blocking of E. histolytica GlcNAc-phosphatidylinositol deacetylase expression: effect on cell proliferation, endocytosis, and adhesion to target cells

2005

Vats, D.; Vishwakarma, R.A.; Bhattacharya, S.; Bhattacharya, A.

Infect. Immun.

8381-8392

665504

14742432

Subcellular localization and targeting of N-acetylglucosaminyl phosphatidylinositol de-N-acetylase, the second enzyme in the glycosylphosphatidylinositol biosynthetic pathway

2004

Pottekat, A.; Menon, A.K.

J. Biol. Chem.

279

15743-15751

665630

15817455

The N-acetyl-D-glucosaminylphosphatidylinositol De-N-acetylase of glycosylphosphatidylinositol biosynthesis is a zinc metalloenzyme

2005

Urbaniak, M.D.; Crossman, A.; Chang, T.; Smith, T.K.; van Aalten, D.M.; Ferguson, M.A.

J. Biol. Chem.

280

22831-22838

684885

18029261

An efficient method to express GPI-anchor proteins in insect cells

2008

Shams-Eldin, H.; Azzouz, N.; Niehus, S.; Smith, T.K.; Schwarz, R.T.

Biochem. Biophys. Res. Commun.

365

657-663

719266

22222041

Inhibitors incorporating zinc-binding groups target the GlcNAc-PI de-N-acetylase in Trypanosoma brucei, the causative agent of African sleeping sickness

2012

Abdelwahab, N.Z.; Crossman, A.T.; Sullivan, L.; Ferguson, M.A.; Urbaniak, M.D.

Chem. Biol. Drug Des.

270-278

719943

21118807

N-Acetyl-D-glucosaminylphosphatidylinositol de-N-acetylase from Entamoeba histolytica: metal alters catalytic rates but not substrate affinity

2011

Ashraf, M.; Yadav, B.; Perinthottathil, S.; Kumar, K.S.; Vats, D.; Muthuswami, R.; Komath, S.S.

J. Biol. Chem.

286

2543-2549

734251

23341455

Catalysis by N-acetyl-D-glucosaminylphosphatidylinositol de-N-acetylase (PIG-L) from Entamoeba histolytica: new roles for conserved residues

2013

Ashraf, M.; Sreejith, P.; Yadav, U.; Komath, S.S.

J. Biol. Chem.

288

7590-7595

734824

24519084

Probing the substrate specificity of Trypanosoma brucei GlcNAc-PI de-N-acetylase with synthetic substrate analogues

2014

Capes, A.S.; Crossman, A.; Urbaniak, M.D.; Gilbert, S.H.; Ferguson, M.A.; Gilbert, I.H.

Org. Biomol. Chem.

1919-1934

756513

26476127

In silico drug re-purposing against African sleeping sickness using GlcNAc-PI de-N-acetylase as an experimental target

2015

Rashmi, M.; Swati, D.

Comput. Biol. Chem.

87-94

756746

29945236

Characterising N-acetylglucosaminylphosphatidylinositol de-N-acetylase (CaGpi12), the enzyme that catalyses the second step of GPI biosynthesis in Candida albicans

2018

Yadav, U.; Rai, K.T.; Sethi, S.C.; Chandraker, A.; Khan, M.A.; Komath, S.S.

FEMS Yeast Res.

foy067