Ligand view of N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine (9225 - GIVLTTJNORAZON-RLADFVFXSA-N)

C₆₇H₁₂₁N₃O₂₆

N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine

GIVLTTJNORAZON-RLADFVFXSA-N

KEGG

Glycosphingolipid biosynthesis - ganglio series

MetaCyc

ganglio-series glycosphingolipids biosynthesis

2.4.1.62

UDPgalactose + N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine = UDP + D-galactosyl-1,3-beta-N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-D-glucosyl-N-acylsphingosine

489313, 489224, 489225, 489308, 489315, 489316

-

2.4.1.92

UDP-N-acetyl-D-galactosamine + 1-O-[O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1-4)-O-[N-acetyl-alpha-neuraminosyl-(2-3)]-O-beta-D-galactopyranosyl-(1-4)-beta-D-glucopyranosyl]-ceramide = ?

676275

-

3.2.1.52

ganglioside GM2 + H2O = ganglioside GM3 + N-acetyl-beta-D-galactosamine

-

UDP-galactose + ganglioside GM2 = UDP + galactosyl-beta-1,3-ganglioside GM2

638321, 489314

-

2.4.1.179

UDP-galactose + ganglioside GM2 = UDP + beta-D-galactosyl-1,3-ganglioside GM2

-

UDP-N-acetyl-D-galactosamine + 1-O-[O-2-(acetylamino)-2-deoxy-beta-D-galactopyranosyl-(1-4)-O-[N-acetyl-alpha-neuraminosyl-(2-3)]-O-beta-D-galactopyranosyl-(1-4)-beta-D-glucopyranosyl]-ceramide = ?

676275

-

2.4.3.2

CMP-N-acetyl-beta-neuraminate + ganglioside GM2 = ?

-

ganglioside GM2 + H2O = ?

693589

-

3.5.1.69

ganglioside GM2 + H2O = fatty acid + lyso-GM2-ganglioside

-

CMP-N-acetylneuraminate + asialoGM2 = CMP + GM2

-

-

-

0.04

-

171152

136606

6222051

Neutral beta-N-acetylhexosaminidases of rat brain. Purification and enzymatic and immunological characterization

1983

Izumi, T.; Suzuki, K.

J. Biol. Chem.

258

6991-6999

171152

4711815

The purification and properties of a mammalian neuraminidase (sialidase)

1973

Tallman J.F.; Brady, R.O.

Biochim. Biophys. Acta

293

434-443

171986

3360750

A novel glycosphingolipid hydrolyzing enzyme, glycosphingolipid ceramide deacylase, which cleaves the linkage between the fatty acid and sphingosine base in glycosphingolipids

1988

Hirabayashi, Y.; Kimura, M.; Matsumoto, M.; Yamamoto, K.; Kadowaki, S.; Tochikura, T.

J. Biochem.

103

1-4

288938

7592649

A novel enzyme that cleaves the N-acyl linkage of ceramides in various glycospingolipids as well as sphingomyelin to produce their lyso forms

1995

Ito, M.; Kurita, T.; Kita, K.

J. Biol. Chem.

41

24370-24374

393654

2961751

A GM2-specific beta-hexosaminidase from the roe of striped mullet (Mugil cephalus)

1988

DeGaspari, R.; Li, S.C.; Li, Y.T.

J. Biol. Chem.

263

1325-1328

393663

6223923

Purification and characterization of beta-N-acetylhexosaminidase from the ascidian, Halocynthia roretzi

1983

Uda, Y.; Itoh, T.

J. Biochem.

93

847-855

393678

5506280

Studies on the glycosidases of jack bean meal, III. Crystallisation and properties of beta-N-acetylhexosaminidase

1970

Li, S.C.; Li, Y.T.

J. Biol. Chem.

245

5153-5160

393693

1404373

Crystallization of human beta-N-acetylhexosaminidase B

1992

Church, W.B.; Swenson, L.; James, M.N.G.

J. Mol. Biol.

227

577-580

489224

11342220

Characterization of the human UDP-galactose:ceramide galactosyltransferase gene promoter

2001

Tencomnao, T.; Yu, R.K.; Kapitonov, D.

Biochim. Biophys. Acta

1517

416-423

489225

8521863

UDP galactose:ceramide galactosyltransferase and glutamate/aspartate transporter. Copurification, separation and characterization of the two glycoproteins

1995

Schulte, S.; Stoffel, W.

Eur. J. Biochem.

233

947-953

489303

3449449

Stimulation of uridine diphosphate-galactose: ceramide galactosyl transferase by certain soluble protein factor in rat brain cytosol

1987

Sanyal, S.N.

Indian J. Exp. Biol.

25

606-612

489304

665383

UDP-galactose: ceramide galactosyltransferase. Kinetic properties and effect of detergents and phospholipids on the partially purified enzyme of rat brain

1978

Neskovic, N.M.; Mandel, P.; Gatt, S.

Adv. Exp. Med. Biol.

101

613-630

489305

5842076

Conversion of Tay-Sachs ganglioside to monosialoganglioside by brain uridine diphosphate D-galactose: glycolipid galactosyltransferase

1965

Basu, S.; Kaufman, B.; Roseman, S.

J. Biol. Chem.

240

4115-4117

489306

5484669

Frog brain uridine diphosphate galactose-N-acetylgalactosaminyl-N-acetylneuraminylgalactosylglucosylceramide galactosyltransferase

1970

Yip, M.C.M.; Dain, J.A.

Biochem. J.

118

247-252

489307

4987145

The enzymic synthesis of ganglioside. II. UDP-galactose: N-acetylgalactosaminyl-(N-acetylneuraminyl)galactosyl-glucosyl-ceramide galactosyltransferase in rat brain

1970

Bellman Yip, G.; Dain, J.A.

Biochim. Biophys. Acta

206

252-260

489308

6136408

Ganglioside biosynthesis in rat liver. Characterization of UDPgalactose--glucosylceramide galactosyltransferase and UDPgalactose-GM2 galactosyltransferase

1983

Senn, H.J.; Wagner, M.; Decker, K.

Eur. J. Biochem.

135

231-236

489309

618873

Isolation and partial characterization of an endogenous inhibitor of ceramide glycosyltransferases from rat brain

1978

Costantino-Ceccarini, E.; Suzuki, K.

J. Biol. Chem.

253

340-342

489310

7521399

Isolation, characterization, and expression of cDNA clones that encode rat UDP-galactose:ceramide galactosyltransferase

1994

Stahl, N.; Jurevics, H.; Morell, P.; Suzuki, K.; Popko, B.

J. Neurosci. Res.

38

234-242

489312

8748162

Purification, properties, and immunological characterization of GalT-3 (UDP-galactose: GM2 ganglioside, beta1-3 galactosyltransferase) from embryonic chicken brain

1995

Ghosh, S.; Kyle, J.W.; Dastgheib, S.; Daussin, F.; Li, Z.; Basu, S.

Glycoconjugate J.

12

838-847

489313

9748263

UDP-galactose:ceramide galactosyltransferase is a class I integral membrane protein of the endoplasmic reticulum

1998

Sprong, H.; Kruithof, B.; Leijendekker, R.; Slot, J.W.; Van Meer, G.; Van Der Sluijs, P.

J. Biol. Chem.

273

25880-25888

489314

9582303

A family of human beta3-galactosyltransferases. Characterization of four members of a UDP-galactose:beta-N-acetyl-glucosamine/beta-acetyl-galactosamine beta-1,3-galactosyltransferase family

1998

Amado, M.; Almeida, R.; Carneiro, F.; Levery, S.B.; Holmes, E.H.; Nomoto, M.; Hollingsworth, M.A.; Hassan, H.; Schwientek, T.; Nielsen, P.A.; Bennett, E.P.; Clausen, H.

J. Biol. Chem.

273

12770-12778

489315

10502288

Mouse beta 1,3-galactosyltransferase (GA1/GM1/GD1b synthase): protein characterization, tissue expression, and developmental regulation in neural retina

1999

Daniotti, J.L.; Martina, J.A.; Zurita, A.R.; Maccioni, H.J.

J. Neurosci. Res.

58

318-327

489316

10905635

GM1 synthase depends on N-glycosylation for enzyme activity and trafficking to the Golgi complex

2000

Martina, J.A.; Daniotti, J.L.; Maccioni, H.J.

Neurochem. Res.

25

725-731

489574

5554906

The enzymic synthesis of ganglioside. IV. UDP-N-acetylgalactosamine: (N-acetylneuraminyl)-galactosylglucosyl ceramide N-acetylgalactosaminyltransferase in rat brain

1971

Dicesare, J.L.; Dain, J.A.

Biochim. Biophys. Acta

231

385-393

489575

6118272

Ganglioside biosynthesis in rat liver. Characterization of UDP-N-acetylgalactosamine - GM3 acetylgalactosaminyltransferase

1981

Senn, H.J.; Cooper, C.; Warnke, P.C.; Wagner, M.; Decker, K.

Eur. J. Biochem.

120

59-67

489578

8245020

Purification and characterization of UDP-N-acetylgalactosamine GM3/GD3 N-acetylgalactosaminyltransferase from mouse liver

1993

Hashimoto, Y.; Sekine, M.; Iwasaki, K.; Suzuki, A.

J. Biol. Chem.

268

25857-25864

489579

3140234

Both GA2, GM2, and GD2 synthases and GM1b, GD1a, and GT1b synthases are single enzymes in Golgi vesicles from rat liver

1988

Pohlentz, G.; Klein, D.; Schwarzmann, G.; Schmitz, D.; Sandhoff, K.

Proc. Natl. Acad. Sci. USA

85

7044-7048

489581

3115968

Biosynthesis of monosulfogangliotriaosylceramide and GM2 by N-acetylgalactosaminyltransferase from rat brain

1987

Nagai, K.I.; Ishizuka, I.

J. Biochem.

101

1115-1127

489582

3109491

Purification and properties of GM2 synthase, UDP-N-acetylgalactosamine: GM3 beta-N-acetylgalactosaminyltransferase from rat liver

1987

Yanagisawa, K.; Taniguchi, N.; Makita, A.

Biochim. Biophys. Acta

919

213-220

587166

3115774

Substrate specificity of GM2 and GD3 synthase of Golgi vesicles derived from rat liver

1987

Klein, D.; Pohlentz, G.; Schwarzmann, G.; Sandhoff, K.

Eur. J. Biochem.

167

417-424

587167

3113445

Oligosialogangliosides inhibit GM2- and GD3-synthesis in isolated Golgi vesicles from rat liver

1987

Yusuf, H.K.M.; Schwarzmann, G.; Pohlentz, G.; Sandhoff, K.

Biol. Chem. Hoppe-Seyler

368

455-462

638321

3924026

Co-purification of galactosyltransferases from chick-embryo liver

1985

Furukawa, K.; Roth, S.

Biochem. J.

227

573-582

638376

3129295

Characterization and specific assay for a galactoside beta-3-galactosyltransferase of human kidney

1988

Bailly, P.; Piller, F.; Cartron, J.P.

Eur. J. Biochem.

173

417-422

654853

12527415

A single site in human beta-hexosaminidase A binds both 6-sulfate-groups on hexosamines and the sialic acid moiety of GM2 ganglioside

2003

Sharma, R.; Bukovac, S.; Callahan, J.; Mahuran, D.

Biochim. Biophys. Acta

1637

113-118

657431

12939050

Trypanosoma evansi sialidase: surface localization, properties and hydrolysis of ghost red blood cells and brain cells-implications in trypanosomiasis

2003

Nok, A.J.; Nzelibe, H.C.; Yako, S.K.

Z. Naturforsch. C

58

594-601

666083

16698036

Crystallographic Structure of Human beta-Hexosaminidase A: Interpretation of Tay-Sachs Mutations and Loss of G(M2) Ganglioside Hydrolysis

2006

Lemieux, M.J.; Mark, B.L.; Cherney, M.M.; Withers, S.G.; Mahuran, D.J.; James, M.N.

J. Mol. Biol.

359

913-929

676275

16358009

Chemo-enzymatic synthesis of GM3 and GM2 gangliosides containing a truncated ceramide functionalized for glycoconjugate synthesis and solid phase applications

2006

Jacques, S.; Rich, J.R.; Ling, C.; Bundle, D.R.

Org. Biomol. Chem.

4

142-154

693589

18974962

Bioluminescent assay for sphingolipid ceramide N-deacylase using Vibrio harveyi dark mutant M-17

2008

Cho, K.W.

J. Microbiol.

46

585-589

745249

438198

Enzymatic characterization of beta D-galactoside alpha2 leads to 3 sialyltransferase from porcine submaxillary gland

1979

Rearick, J.I.; Sadler, J.E.; Paulson, J.C.; Hill, R.L.

J. Biol. Chem.

254

4444-4451

751281

25984755

Pyrimethamine derivatives insight into binding mechanism and improved enhancement of mutant beta-N-acetylhexosaminidase activity

2015

Tropak, M.B.; Zhang, J.; Yonekawa, S.; Rigat, B.A.; Aulakh, V.S.; Smith, M.R.; Hwang, H.J.; Ciufolini, M.A.; Mahuran, D.J.

J. Med. Chem.

58

4483-4493

-

Ligand N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine

Basic Ligand Information

Roles as Enzyme Ligand

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

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

Substrate in Enzyme-catalyzed Reactions (14 results)

Product in Enzyme-catalyzed Reactions (4 results)

Inhibitor in Enzyme-catalyzed Reactions (3 results)

Enzyme Kinetic Parameters

K_M Value (6 results)

References & Links

Literature References (40)

Links to other databases for N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine

Ligand N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine

Basic Ligand Information

Roles as Enzyme Ligand

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

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

Substrate in Enzyme-catalyzed Reactions (14 results)

Product in Enzyme-catalyzed Reactions (4 results)

Inhibitor in Enzyme-catalyzed Reactions (3 results)

Enzyme Kinetic Parameters

KM Value (6 results)

References & Links

Literature References (40)

Links to other databases for N-acetyl-D-galactosaminyl-(N-acetylneuraminyl)-D-galactosyl-1,4-beta-D-glucosyl-N-acylsphingosine

K_M Value (6 results)