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G2392

Sigma-Aldrich

Disialoganglioside GD1a from bovine brain

≥95% (TLC), lyophilized powder

Synonym(s):

Ganglioside GD1a, disialo from bovine brain

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About This Item

CAS Number:
12707-58-3
Beilstein:
6228822
MDL number:
MFCD00130960
UNSPSC Code:
12352200
NACRES:
NA.77

Quality Level

200

Assay

≥95% (TLC)

form

lyophilized powder

solubility

DMSO: soluble

storage temp.

−20°C

InChI

1S/C86H152N4O39.2Na/c1-6-8-10-12-14-16-18-20-22-24-26-28-30-32-34-36-51(100)50(90-60(105)37-35-33-31-29-27-25-23-21-19-17-15-13-11-9-7-2)46-118-80-69(111)67(109)72(57(43-94)120-80)123-82-71(113)78(129-86(84(116)117)39-53(102)62(88-48(4)98)77(128-86)65(107)55(104)41-92)74(59(45-96)122-82)124-79-63(89-49(5)99)75(66(108)56(42-93)119-79)125-81-70(112)68(110)73(58(44-95)121-81)126-85(83(114)115)38-52(101)61(87-47(3)97)76(127-85)64(106)54(103)40-91;;/h34,36,50-59,61-82,91-96,100-104,106-113H,6-33,35,37-46H2,1-5H3,(H,87,97)(H,88,98)(H,89,99)(H,90,105)(H,114,115)(H,116,117);;/q;2*+1/p-2/b36-34+;;/t50-,51+,52?,53?,54-,55-,56?,57?,58?,59?,61+,62+,63?,64-,65-,66?,67?,68?,69?,70?,71?,72?,73?,74?,75?,76?,77?,78?,79?,80?,81?,82?,85?,86?;;/m0../s1

InChI key

CWLDKTAXQZEVQN-CUEXFKMESA-L

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Amino Acid Sequence

Cer-Glc-Gal(NeuAc)-GalNAc-Gal-NeuAc

General description

Gangliosides are in the neuronal cell membranes and endoplasmic reticulum. They consist of a sialylated polysaccharide chain linked via β-glycosidic linkage to ceramide. They are also located in body fluids and plasma. GD1a consists of a neutral tetrasaccharide core with one sialic acid on the internal galactose and another sialic acid on the non-reducing terminal galactose.

Application

Disialoganglioside GD1a from bovine brain has been used:
  • as a receptor for the detection of murine norovirus-1 (MNV-1) by RT-PCR
  • as a glycolipid to study the interaction between protein human endogenous retrovirus W family pHERV-W ENV and glycolipids by enzyme-linked immunosorbent assay (ELISA)
  • as a reference standard to analyze the ganglioside signatures of prostate cancer cells by high-performance liquid chromatography

Biochem/physiol Actions

Gangliosides are involved in cellular functions such as the differentiation of neurons, formation of axons, synapses, cell proliferation, differentiation, adhesion, and cell death. In addition, gangliosides form microdomains on the outer surface of the cell membranes that are involved in signal transduction and help in the formation of dendrites. Gangliosides act as Ca2+ binding co-factors during synaptic transmission.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000340085
0000318967
0000318967
0000340085
0000274152

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S Yamaguchi et al.
Glycoconjugate journal, 14(6), 707-714 (1997-10-23)
Gangliosides are known to be differentiation-inducing molecules in mammalian stem cells. We studied the interaction between the molecular structure of glycosphingolipids (GSLs) and their promoting mechanisms of the phagocytic processes in human polymorphonuclear leukocytes (PMN). The effect of various gangliosides
Molecular analysis of cross-reactive anti-myosin/anti-streptococcal mouse monoclonal antibodies
Nadja M J, et al.
Molecular Immunology, 37(15), 901-913 (2000)
Gangliosides as Immunomodulators
Miroslava P, et al.
Advances in Experimental Medicine and Biology, 195?203-195?203 (2000)
Biosynthesis of the major brain gangliosides GD1a and GT1b
Elizabeth R S, et al.
Glycobiology, 22(10), 1289?1301-1289?1301 (2012)
K F Meiri et al.
Journal of neurochemistry, 62(1), 291-299 (1994-01-01)
Phosphorylation of the nervous system-specific protein GAP-43 in growth cones in vivo increases as the growth cones near their targets, at a time when the gangliosides GM1 and GD1a are being accumulated in the growth cone membrane, thus raising the
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