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Ligand lactosylceramide

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (10 results)

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Show Natural Substrate (10 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.206

UDP-N-acetyl-D-glucosamine + lactosylceramide = UDP + N-acetyl-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide

638230, 638233, 638234, 638232, 638231

-

2.4.1.228

UDP-galactose + beta-D-galactosyl-(1,4)-D-glucosylceramide = UDP + alpha-D-galactosyl-(1,4)-beta-D-galactosyl-(1,4)-D-glucosylceramide

659273

-

2.4.1.228

UDP-galactose + beta-D-galactosyl-(1-4)-D-glucosylceramide = UDP + alpha-D-galactosyl-(1-4)-beta-D-galactosyl-(1-4)-D-glucosylceramide

488980, 488981, 488982, 488983, 488985, 488979, 488984

-

2.4.1.228

UDP-galactose + lactosylceramide = UDP + globotriaosylceramide

703661, 703901

-

2.4.3.9

CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide = CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide

764220, 736209

-

2.4.3.9

CMP-N-acetylneuraminate + lactosylceramide = CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosyl-ceramide

672358, 673509, 674638

-

2.4.3.9

CMP-N-acetylneuraminate + lactosylceramide = CMP + ganglioside GM4

736209

-

2.4.3.9

CMP-N-acetylneuraminate + lactosylceramide = CMP + N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide

638776, 638785

-

2.4.1.228

3 entries

2.4.3.9

4 entries

3.2.1.18

lactosyl-ceramide + H2O = ?

730792

-

3.2.1.62

lactosylceramide + H2O = beta-D-glucose + galactosylceramide

208758

-

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

2.4.1.274

UDP-galactose + beta-D-glucosyl-(1<->1)-ceramide = UDP + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide

0

-

2.4.1.274

UDP-alpha-D-galactose + glucosylceramide = UDP + lactosylceramide

0

-

2.4.1.274

2 entries

3.2.1.22

D-galactosyl-D-galactosyl-D-glucosyl-N-acylsphingosine + H2O = lactosyl-N-acylsphingosine + D-galactose

0

-

Substrate in Enzyme-catalyzed Reactions (30 results)

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Show Substrate (30 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.149

UDP-N-acetyl-D-glucosamine + lactosylceramide = ?

638606

-

2.4.1.149

UDP-N-acetylglucosamine + lactosylceramide = ?

638576

-

2.4.1.149

2 entries

2.4.1.179

UDP-galactose + lactosylceramide = ?

488980, 638376

-

2.4.1.206

UDP-N-acetyl-D-glucosamine + beta-D-galactosyl-(1-4)-beta-D-glucosyl-(1-1)-ceramide = UDP + N-acetyl-beta-D-glucosaminyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide

687972

-

2.4.1.206

UDP-N-acetyl-D-glucosamine + D-galactosyl-1,4-beta-D-glucosylceramide = UDP + N-acetyl-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide

638235, 638236, 638234, 638230, 638231, 638232, 638233

-

2.4.1.206

UDP-N-acetyl-D-glucosamine + lactosylceramide = UDP + N-acetyl-D-glucosaminyl-1,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide

638230, 638233, 638234, 638232, 638231

-

2.4.1.228

UDP-galactose + beta-D-galactosyl-(1,4)-D-glucosylceramide = UDP + alpha-D-galactosyl-(1,4)-beta-D-galactosyl-(1,4)-D-glucosylceramide

659273

-

2.4.1.228

UDP-galactose + beta-D-galactosyl-(1-4)-D-glucosylceramide = UDP + alpha-D-galactosyl-(1-4)-beta-D-galactosyl-(1-4)-D-glucosylceramide

488980, 488981, 488982, 488983, 488985, 488979, 488984

-

2.4.1.228

UDP-galactose + lactosylceramide = UDP + globotriaosylceramide

488983, 488985, 702866, 703661, 703901, 488984, 488980, 488979, 488982, 488981

-

2.4.1.206

3 entries

2.4.1.228

3 entries

2.4.1.274

UDP-galactose + lactosylceramide = ?

715415

-

2.4.1.37

beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide + UDP-GalNAc = ?

720246

-

2.4.1.37

UDP-alpha-D-galactose + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide = UDP + alpha-D-galactosyl-(1->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide

720246, 719219

-

2.4.1.69

GDP-beta-L-fucose + lactosylceramide = ?

489359

-

2.4.1.69

GDP-L-fucose + lactosylceramide = GDP + ?

489359

-

2.4.1.92

UDP-N-acetyl-alpha-D-galactosamine + lactosylceramide = UDP-N-acetyl-alpha-D-galactosamine + ganglioside GA2

746327

-

2.4.1.92

UDP-N-acetyl-D-galactosamine + lactosylceramide = UDP + GA2-ganglioside

489579

-

2.4.1.37

2 entries

2.4.1.69

2 entries

2.4.1.92

2 entries

2.4.3.1

CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-beta-D-glucosylceramide = CMP + alpha-N-acetylneuraminyl-2,6-beta-D-galactosyl-1,4-beta-D-glucosylceramide

636887, 636888

-

2.4.3.9

CMP-N-acetylneuraminate + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide = CMP + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide

764220, 736209

-

2.4.3.9

CMP-N-acetylneuraminate + beta-D-galactosyl-1,4-beta-D-glucosylceramide = CMP + N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide

723516, 636879, 638776, 489583, 638793, 636877, 637739, 636888, 637736, 637737, 637742, 638779, 638781, 638782, 638788, 638792, 638785, 638783, 638780, 638791

-

2.4.3.9

CMP-N-acetylneuraminate + lactosylceramide = ?

738726, 705676

-

2.4.3.9

CMP-N-acetylneuraminate + lactosylceramide = CMP + alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosyl-ceramide

672358, 674638, 721691, 673509

-

2.4.3.9

CMP-N-acetylneuraminate + lactosylceramide = CMP + ganglioside GM4

736209

-

2.4.3.9

CMP-N-acetylneuraminate + lactosylceramide = CMP + N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide

658140, 638776, 638785

-

2.4.3.9

CMP-Neu5Ac + lactosylceramide = ?

703916

-

2.4.3.9

7 entries

2.8.2.11

lactosylceramide + 3'-phosphoadenylylsulfate = lactosylceramide sulfate + adenosine 3',5'-bisphosphate

645700, 645703

-

3.2.1.123

lactosylceramide + H2O = ?

732295

-

3.2.1.18

lactosyl-ceramide + H2O = ?

730792

-

3.2.1.23

lactosyl ceramide + H2O = ?

703719, 171319, 171321, 171322

-

3.2.1.62

lactosylceramide + H2O = beta-D-glucose + galactosylceramide

208758

-

3.5.1.69

lactosylceramide + H2O = ?

288938

-

Product in Enzyme-catalyzed Reactions (5 results)

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Show Product (5 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.274

UDP-galactose + beta-D-glucosyl-(1<->1)-ceramide = UDP + beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide

0

-

2.4.1.274

UDP-alpha-D-galactose + glucosylceramide = UDP + lactosylceramide

0

-

2.4.1.274

2 entries

3.2.1.22

D-galactosyl-D-galactosyl-D-glucosyl-N-acylsphingosine + H2O = lactosyl-N-acylsphingosine + D-galactose

0

-

3.2.1.52

asialo GM2 ganglioside + H2O = lactosylceramide

393663, 136606

-

3.2.1.53

GalNAc-beta-1,4-Gal-beta-1,4-Glc-beta-1,1-Cer = GalNAc + Gal-beta-1,4-Glc-beta-1,1-Cer

0

-

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.1.62

presence of lactosylceramide is required for B3GALT4 to transfer galalctose to glycosylphosphatidylinositol

757755

-

Inhibitor in Enzyme-catalyzed Reactions (2 results)

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Show Inhibitors (2 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.4.3.2

inhibits reaction with GM1a

637737

-

3.2.1.46

-

171513

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (6 results)

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Show Turnover Number (6 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.4.1.37

0.15

-

mutant C89S/C196S/C209S, pH 7.0, temperature not specified in the publication, co-substrate: donor UDP-GalNAc

720246

2.4.1.37

0.41

-

deletion construct with amino acids 68-354, pH 7.0, temperature not specified in the publication, co-substrate: donor UDP-GalNAc

720246

2.4.1.37

0.7

-

mutant C80S/C196S, pH 7.0, temperature not specified in the publication, co-substrate: donor UDP-GalNAc

720246

2.4.1.37

5.6

-

mutant C80S/C196S, pH 7.0, temperature not specified in the publication, co-substrate: donor UDP-alpha-D-galactose

720246

2.4.1.37

7.3

-

deletion construct with amino acids 68-354, pH 7.0, temperature not specified in the publication, co-substrate: donor UDP-alpha-D-galactose

720246

2.4.1.37

8

-

mutant C89S/C196S/C209S, pH 7.0, temperature not specified in the publication, co-substrate: donor UDP-alpha-D-galactose

720246

2.4.1.37

6 entries

K_M Value (25 results)

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Show KM Value (25 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.4.1.179

2.5

-

-

638376

2.4.1.206

0.021

-

cerebellum microsomes

638232

2.4.1.228

0.0013

-

-

488983

2.4.1.228

0.006

-

-

488979

2.4.1.228

0.0545

-

-

488985

2.4.1.228

0.445

-

-

488984

2.4.1.37

0.032

-

mutant C80S/C196S, pH 7.0, temperature not specified in the publication, donor UDP-alpha-D-galactose

720246

2.4.1.37

0.055

-

deletion construct with amino acids 68-354, pH 7.0, temperature not specified in the publication, donor UDP-alpha-D-galactose

720246

2.4.1.37

0.2

-

mutant C89S/C196S/C209S, pH 7.0, temperature not specified in the publication, donor UDP-GalNAc

720246

2.4.1.37

0.3

-

deletion construct with amino acids 68-354, pH 7.0, temperature not specified in the publication, donor UDP-GalNAc

720246

2.4.1.37

0.3

-

mutant C80S/C196S, pH 7.0, temperature not specified in the publication, donor UDP-GalNAc

720246

2.4.1.37

0.35

-

mutant C89S/C196S/C209S, pH 7.0, temperature not specified in the publication, donor UDP-alpha-D-galactose

720246

2.4.1.69

0.052

-

recombinant enzyme

489359

2.4.1.69

0.068

-

-

489359

2.4.1.69

0.068

-

recombinant enzyme

489359

2.4.3.9

0.00011

-

-

638780

2.4.3.9

0.035

-

-

637739

2.4.3.9

0.068

-

-

637737

2.4.3.9

0.075

-

-

636877

2.4.3.9

0.08

-

-

637736, 638783

2.4.3.9

0.0815

-

-

638776

2.4.3.9

0.101

-

-

705676

2.4.3.9

0.11

-

-

638785

2.4.1.228

4 entries

2.4.1.37

6 entries

2.4.1.69

3 entries

2.4.3.9

8 entries

3.2.1.23

5.88

-

-

171322

3.2.1.62

0.27

-

-

208758

References & Links

Literature References (73)

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Show Reference (73 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

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

171319

-

beta-Galactosidase from rat brain

1969

Gatt, S.

Methods Enzymol.

14

156-161

171321

26842

beta-Galactosidase from bovine testes

1978

Distler, J.J.; Jourdian, G.W.

Methods Enzymol.

50

514-520

171322

9384

Purification and characterization of beta-N-acetylhexosaminidases and beta-galactosidase from Streptococcus 6646 K

1976

Kiyohara, T.; Terao, T.; Shioiri-Nakano, K.; Osawa, T.

J. Biochem.

80

9-17

171513

4738302

The inhibitor-sensitive sites of galactosyl ceramide galactosidase

1973

Arora, R.C.; Lin, Y.N.; Radin, N.S.

Arch. Biochem. Biophys.

156

77-83

208758

6790523

The glycosylceramidase in the murine intestine. Purification and substrate specificity

1981

Kobayashi, T.; Suzuki, K.

J. Biol. Chem.

256

7768-7773

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

393663

6223923

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

1983

Uda, Y.; Itoh, T.

J. Biochem.

93

847-855

488979

3921539

Purification and properties of rat liver globotriaosylceramide synthase, UDP-galactose:lactosylceramide alpha1-4-galactosyltransferase

1985

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

J. Biol. Chem.

260

4908-4913

488980

3099784

Identification of UDP-galactose:lactose (lactosylceramide) alpha-4 and beta-3 galactosyltransferases in human kidney

1986

Bailly, P.; Piller, F.; Cartron, J.P.; Leroy, Y.; Fournet, B.

Biochem. Biophys. Res. Commun.

141

84-91

488981

3089222

Studies on the human blood group P system: an existence of UDP-Gal: lactosylceramide alpha 1 -> 4 galactosyltransferase in the small p type cells

1986

Iizuka, S.; Chen, S.H.; Yoshida, A.

Biochem. Biophys. Res. Commun.

137

1187-1195

488982

2497776

Glycolipid glycosyltransferases in human embryonal carcinoma cells during retinoic acid induced differentiation

1989

Chen, C.; Fenderson, B.A.; Andrews, P.W.; Hakomori, S.

Biochemistry

28

2229-2238

488983

8595260

alpha-1,4Galactosyltransferase activity and Gbeta3Cer expression in human leukemia/lymphoma cell lines

1995

Stults, C.L.M.; Larsen, R.D.; Macher, B.A.

Glycoconj. J.

12

680-689

488984

7943326

Developmentally regulated Gb3 galactosyltransferase and alpha-galactosidase determine Shiga toxin receptors in intestine

1994

Mobassaleh, M.; Koul, O.; Mishra, K.; McCluer, R.H.; Keusch, G.T.

Am. J. Physiol.

267

G618-G624

488985

10748143

Molecular cloning of globotriaosylceramide/CD77 synthase, a glycosyltransferase that initiates the synthesis of Globo series glycosphingolipids

2000

Kojima, Y.; Fukumoto, S.; Furukawa, K.; Okajima, T.; Wiels, J.; Yokoyama, K.; Suzuki, Y.; Urano, T.; Ohta, M.; Furukawa, K.

J. Biol. Chem.

275

15152-15156

489359

-

Molecular cloning, chromosomal assignment and tissue-specific expression of a murine alpha-(1,2)fucosyltransferase expressed in thymic and epididymal epithelial cells

1997

Domino, S.E.; Hiraiwa, N.; Lowe, J.B.

Biochem. J.

327

105-115

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

489583

12234191

Regulation of ganglioside biosynthesis by enzyme complex formation of glycosyltransferases

2002

Bieberich, E.; MacKinnon, S.; Silva, J.; Li, D.D.; Tencomnao, T.; Irwin, L.; Kapitonov, D.; Yu, R.K.

Biochemistry

41

11479-11487

636877

3718965

Effects of lectin activation on sialyltransferase activities in human lymphocytes

1986

Basu, S.K.; Whisler, R.L.; Yates, A.J.

Biochemistry

25

2577-2581

636879

3838172

Biosynthesis in vitro of disialosylneolactotetraosylceramide by a solubilized sialyltransferase from embryonic chicken brain

1985

Higashi, H.; Basu, M.; Basu, S.

J. Biol. Chem.

260

824-828

636887

2460092

Purification and characterization of an endogenous inhibitor of the sialyltransferase CMP-N-acetylneuraminate: lactosylceramide alpha 2,6-N-acetylneuraminyltransferase (EC 2.4.99.-)

1988

Albarracin, I.; Lassaga, F.E.; Caputto, R.

Biochem. J.

254

559-565

636888

8158143

Activities of five different sialyltransferases in fish and rat brains

1994

Freischutz, B.; Saito, M.; Rahmann, H.; Yu, R.K.

J. Neurochem.

62

1965-1973

637736

3769920

Ganglioside biosynthesis in rat liver. Characterization of three sialyltransferases

1986

Busam, K.; Decker, K.

Eur. J. Biochem.

160

23-30

637737

1991463

Substrate specificity of alpha 2->3-sialyltransferases in ganglioside biosynthesis of rat liver Golgi

1991

Iber, H.; van Echten, G.; Sandhoff, K.

Eur. J. Biochem.

195

115-120

637739

4022

Butyrate-induced glycolipid biosynthesis in HeLa cells: properties of the induced sialyltransferase

1976

Fishman, P.H.; Bradley, R.M.; Henneberry, R.C.

Arch. Biochem. Biophys.

172

618-626

637742

2120225

Sub-Golgi distribution in rat liver of CMP-NeuAc GM3- and CMP-NeuAc:GT1b alpha 2->8sialyltransferases and comparison with the distribution of the other glycosyltransferase activities involved in ganglioside biosynthesis

1990

Trinchera, M.; Pirovano, B.; Ghidoni, R.

J. Biol. Chem.

265

18242-18247

638230

1825612

Glycolipids and glycosyltransferases in permanent cell lines established from human medulloblastomas

1991

Gottfries, J.; Percy, A.K.; Mansson, J.E.; Fredman, P.; Wikstrand, C.J.; Friedman, H.S.; Bigner, D.D.; Svennerholm, L.

Biochim. Biophys. Acta

1081

253-261

638231

2960671

Synthesis of type 1 and 2 lacto series glycolipid antigens in human colonic adenocarcinoma and derived cell lines is due to activation of a normally unexpressed beta 1-3N-acetylglucosaminyltransferase

1987

Holmes, E.H.; Hakomori, S.i.; Ostrander, G.K.

J. Biol. Chem.

262

15649-15658

638232

8408027

N-acetylglucosaminyltransferase regulates the expression of neolactoglycolipids including sulfoglucuronylglycolipids in the developing nervous system

1993

Chou, D.K.H.; Jungalwala, F.B.

J. Biol. Chem.

268

21727-21733

638233

10561117

Glycolipid glycosyltransferase activities during early development of Xenopus: effect of retinoic acid

1999

Rossi, F.; Gornati, R.; Rizzo, A.M.; Venturini, L.; Bernadini, G.; Berra, B.

Cell Biol. Int.

23

91-95

638234

8910533

N-acetylglucosaminyl Transferase regulates the expression of sulfoglucuronyl glycolipids in specific cell types in cerebellum during development

1996

Chou, D.K.H.; Jungalwala, F.B.

J. Biol. Chem.

271

28868-28874

638235

11283017

Molecular cloning and characterization of UDP-GlcNAc:lactosylceramide beta1,3-N-acetylglucosaminyltransferase (beta3Gn-T5), an essential enzyme for the expression of HNK-1 and lewis X epitopes on glycolipids

2001

Togayachi, A.; Akashima, T.; Ookubo, R.; Kudo, T.; Nishihara, S.; Iwasaki, H.; Natsume, A.; Mio, H.; Inokuchi, J.i.; Irimura, T.; Sasaki, K.; Narimatsu, H.

J. Biol. Chem.

276

22032-22040

638236

11384981

Cloning of a mouse beta1,3 N-acetylglucosaminyltransferase GlcNAc(beta1,3)Gal(beta1,4)Glc-ceramide synthase gene encoding the key regulator of lacto-series glycolipid biosynthesis

2001

Henion, T.R.; Zhou, D.; Wolfer, D.P.; Jungalwala, F.B.; Hennet, T.

J. Biol. Chem.

276

30261-30269

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

638576

2963590

Characterization of a beta 1-->3-N-acetylglucosaminyltransferase associated with synthesis of type 1 and type 2 lacto-series tumor-associated antigens from the human colonic adenocarcinoma cell line SW403

1988

Holmes, E.H.

Arch. Biochem. Biophys.

260

461-468

638606

6238026

Biosynthesis in vitro of Ii core glycosphingolipids from neolactotetraosylceramide by beta1-3- and beta1-6-N-acetylglucosaminyltransferases from mouse T-lymphoma

1984

Basu, M.; Basu, S.

J. Biol. Chem.

259

12557-12562

638776

8512559

Inhibition of CMP-N-acetylneuraminic acid:lactosylceramide sialyltransferase by nucleotides, nucleotide sugars and nucleotide dialdehydes

1993

Cambron, L.D.; Leskawa, K.C.

Biochem. Biophys. Res. Commun.

193

585-590

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Links to other databases for lactosylceramide

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