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Merck
CN

345743

Disialoganglioside-GD₂ from bovine brain

≥98% (TLC), lyophilized, cell type and antigen marker, Calbiochem®

Synonym(s):

Ganglioside GD2, Disialo, Human Brain, GalNAcβ1,4(Neu5Acα2,8)(Neu5Acα2,03)Galβ1,4Glcβ1,1ʹ Ceramide

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About This Item

Empirical Formula (Hill Notation):
C78H138N4O34
CAS Number:
65988-71-8
Molecular Weight:
1675.94
UNSPSC Code:
12352211
NACRES:
NA.77
MDL number:
MFCD00131133

Key Documents

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Product Name

Ganglioside GD2, Disialo, Human Brain, Ganglioside GD2, Disialo, Human Brain, CAS 65988-71-8, is a highly purified sialic acid-containing glycolipids that is useful as markers of various cell types and antigens.

SMILES string

N([C@H]1[C@@H](O[C@@H]([C@@H]([C@@H]1O)O)CO)O[C@H]2[C@H](O[C@H]([C@@H]([C@H]2O[C@]4(O[C@@H]([C@H]([C@@H](C4)O)N)C(O)C(O)CO[C@]5(O[C@@H]([C@H]([C@@H](C5)O)N)C(O)C(O)CO)C(=O)O)C(=O)O)O)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)OCC(NC(=O)CCCCCCCCCCCCCCCCC)C(O)\C

InChI

1S/C74H134N4O32/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-52(89)78-43(44(84)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)40-101-69-61(95)60(94)63(50(38-81)104-69)106-70-62(96)67(64(51(39-82)105-70)107-68-55(77-42(3)83)59(93)58(92)49(37-80)103-68)110-74(72(99)100)35-46(86)54(76)66(109-74)57(91)48(88)41-102-73(71(97)98)34-45(85)53(75)65(108-73)56(90)47(87)36-79/h30,32,43-51,53-70,79-82,84-88,90-96H,4-29,31,33-41,75-76H2,1-3H3,(H,77,83)(H,78,89)(H,97,98)(H,99,100)/b32-30+/t43?,44?,45-,46-,47?,48?,49-,50-,51-,53+,54+,55-,56?,57?,58+,59-,60-,61-,62-,63-,64+,65+,66+,67-,68+,69-,70+,73-,74+/m1/s1

InChI key

FFILOTSTFMXQJC-QCFYAKGBSA-N

assay

≥98% (TLC)

form

lyophilized

manufacturer/tradename

Calbiochem®

storage condition

OK to freeze

solubility

chloroform/methanol (2:1): soluble

shipped in

ambient

storage temp.

−20°C

Quality Level

100

Related Categories

Disclaimer

Toxicity: Irritant (B)

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Application

Disialoganglioside-GD₂ from bovine brain has been used in GD2 Ganglioside O-Acetylation and to study the role of sialyl-O-acetyltransferase CASD1 on GD2 ganglioside O-acetylation in breast cancer cells. It has also been used in phase I trial to quantify the anti-GD2 response by coating 96-well microtiter plates for the detection of antibodies in serum samples through an enzyme linked immunosorbent assay (ELISA) method.

Features and Benefits

  • Primary Target: Useful as markers of various cell types and antigens
  • Cell permeable: no
  • Product does not compete with ATP
  • Reversible: no

General description

Gangliosides are highly purified sialic acid-containing glycolipids that are useful as markers of various cell types and antigens. Disialoganglioside GD2 is less expressed in normal tissues while predominantly found in the central nervous system, peripheral sensory nerve fibers, dermal melanocytes, lymphocytes, and mesenchymal stem cells. Disialoganglioside GD2 is a tumor-associated antigen and contributes to enhanced tumor cell proliferation, motility, migration, adhesion, and invasion, depending on the tumor type, and resists apoptosis. This tumor marker is implicated in neuroblastomas, melanomas and retinoblastomas.

Other Notes

The molecular weight is based on stearoyl-18:0.

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Sumeyye Cavdarli et al.
Cells, 10(6) (2021-07-03)
The O-acetylated form of GD2, almost exclusively expressed in cancerous tissues, is considered to be a promising therapeutic target for neuroectoderm-derived tumors, especially for breast cancer. Our recent data have shown that 9-O-acetylated GD2 (9-OAcGD2) is the major O-acetylated ganglioside

Articles

Glycosphingolipids

Glycosphingolipids (sometimes called glycolipids) have been found in lower and higher eukaryotic sources. They are composed of a glycan structure attached to a lipid tail that contains the sphingolipid ceramide.

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