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  • 65988-71-8 , GD2-Ganglioside , Disialoganglioside-GD2
65988-71-8 , GD2-Ganglioside , Disialoganglioside-GD2

65988-71-8 , GD2-Ganglioside , Disialoganglioside-GD2

65988-71-8 , GD2-Ganglioside , Disialoganglioside-GD2
Cas:65988-71-8
C78H138N4O34·xNa / 1675.94 (free acid basis)
MFCD01093866

GD2-Ganglioside , Disialoganglioside-GD2

GD2 (shown as sodium salt) has a core trisaccharide structure (GalNAc-b-1,4-Gal-b-1,4-Glc) with its two sialic acids linked b-2,3/b-2,8 to the inner galactose residue and ceramide linked to position 1 on the reducing terminal glucose residue. GD2 ganglioside is expressed at a low concentration in the central nervous system, nerves, skin melanocytes and stem cells in healthy adults. On the other hand, GD2 is overexpressed in a number of tumors, including: neuroblastoma, melanoma, small cell lung carcinoma and brain tumors. Recently, it has been found in low concentrations on breast cancer stem cells (CSC) that possess: self-renewal properties (division without disrupting the undifferentiated state), and tumor-initiating capabilities.  It has been suggested that GD2 ganglioside may be developed as an effective target antigen for CSC immunotherapy (Fleurence, 2017).

GD2 Ganglioside is a glycolipid that is found on the surface of cells and is involved in numerous biological functions. Gangliosides are complex lipids, composed of a hydrophobic tail and a hydrophilic head that is composed of a sialic acid residue and a complex sugar chain. GD2 Ganglioside is a unique glycolipid that is expressed on the surface of human neuroblastoma cells, melanoma cells, and small cell lung cancer cells. It has garnered a considerable amount of attention due to its potential use in various fields of research and industry. This paper aims to provide an in-depth analysis of GD2 Ganglioside, covering its definition, background, physical and chemical properties, synthesis and characterization, analytical methods, biological properties, toxicity and safety in scientific experiments, applications in scientific experiments, current state of research, potential implications in various fields of research and industry, limitations, and future directions.

Definition and Background:

GD2 Ganglioside is a sialylated glycosphingolipid that is present on the surface of certain types of cells. It is composed of a hydrophobic ceramide tail and a hydrophilic head group that contains a sialic acid residue and a complex oligosaccharide chain. The glycosphingolipid has been identified as a tumor-associated antigen that is expressed on the surface of human neuroblastoma cells, melanoma cells, and small cell lung cancer cells. The expression of GD2 Ganglioside is less common in normal cells, which makes it an attractive target for cancer therapies.

Physical and Chemical Properties:

The physical and chemical properties of GD2 Ganglioside are unique. GD2 Ganglioside is a glycosphingolipid that contains a ceramide tail, a sialic acid residue, and an oligosaccharide chain. The molecular weight of GD2 Ganglioside is 2,647.3 g/mol. It is a water-soluble and heat-stable compound. The melting point of GD2 Ganglioside is 163-165°C, and its solubility is dependent on its concentration in the solution.

Synthesis and Characterization:

GD2 Ganglioside can be synthesized through a multistep process involving the use of chemical and enzymatic reactions. The most common method of GD2 Ganglioside synthesis involves the use of sialyltransferases, glycosyltransferases, and ceramide synthases. The characterization of GD2 Ganglioside is typically done using mass spectrometry, nuclear magnetic resonance spectroscopy, and high-performance liquid chromatography.

Analytical Methods:

Analytical methods for GD2 Ganglioside characterization includes mass spectrometry which is used to measure the mass-to-charge ratio of ions, nuclear magnetic resonance spectroscopy which is used to study the interaction between atomic nuclei and an external magnetic field, and high-performance liquid chromatography which is used to separate, identify and quantify organic compounds in a mixture.

Biological Properties:

GD2 Ganglioside has several biological properties, making it a popular target for research. GD2 Ganglioside is a tumor-associated antigen that is expressed on the surface of certain types of tumor cells. It has been identified as a potential target for cancer immunotherapy. GD2 Ganglioside has also been shown to be involved in various biological functions, including cell-cell recognition, signal transduction, and modulation of membrane fluidity.

Toxicity and Safety in Scientific Experiments:

GD2 Ganglioside has been studied for its toxicity and safety in scientific experiments. GD2 Ganglioside has been shown to be relatively safe in animal studies, but there are some concerns about its potential toxicity in humans. GD2 Ganglioside has been shown to be immunogenic and can cause an immune response in some cases.

Applications in Scientific Experiments:

GD2 Ganglioside has numerous applications in scientific experiments. It is used as a marker for tumor cells and is used in cancer immunotherapy. It has also been shown to have potential applications in the field of regenerative medicine, neuroscience, and infectious diseases.

Current State of Research:

The current state of research on GD2 Ganglioside is primarily focused on the development of new cancer treatments and immunotherapies. There is also ongoing research on the potential applications of GD2 Ganglioside in regenerative medicine and neuroscience.

Potential Implications in Various Fields of Research and Industry:

GD2 Ganglioside has potential implications in various fields of research and industry. It has the potential to revolutionize cancer therapy by targeting tumor cells while sparing normal cells. GD2 Ganglioside could also be used in regenerative medicine to help repair damaged tissues and in neuroscience to help understand the complex mechanisms of the human nervous system.

Limitations and Future Directions:

Despite the potential applications of GD2 Ganglioside, there are several limitations that need to be considered. There is still much that is unknown about the downstream effects of GD2 Ganglioside on cellular processes, and there is a need for further research in this area. Additionally, the potential toxicity of GD2 Ganglioside needs to be further investigated, particularly in human studies.

Future research directions for GD2 Ganglioside include the development of more effective cancer immunotherapies, the exploration of its potential applications in regenerative medicine and neuroscience, and the continued investigation of its safety and toxicity in human studies. Furthermore, there is a need for developing more efficient and cost-effective methods for GD2 Ganglioside synthesis and purification. Finally, the advancement of analytical methods for GD2 Ganglioside characterization should be pursued to yield more detailed insight into its biological properties.

In conclusion, GD2 Ganglioside is a unique glycolipid that has potential implications in various fields of research and industry. Its unique biological properties, such as its tumor-associated antigen expression, make it a compelling target for cancer therapy and immunotherapy. However, there is still much that is unknown about its mechanisms of action, and further research is needed to fully understand its potential applications as well as any limitations.

CAS Number65988-71-8
Product NameGD2 Ganglioside
IUPAC Name(2R,4R,5S,6S)-2-[3-[(2S,3S,4R,6S)-6-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-3-amino-6-carboxy-4-hydroxyoxan-2-yl]-2,3-dihydroxypropoxy]-5-amino-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid
Molecular FormulaC74H134N4O32
Molecular Weight1591.9 g/mol
InChIInChI=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 KeyFFILOTSTFMXQJC-QCFYAKGBSA-N
SMILESCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)NC(=O)C)OC4(CC(C(C(O4)C(C(COC5(CC(C(C(O5)C(C(CO)O)O)N)O)C(=O)O)O)O)N)O)C(=O)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
Synonymsganglioside, GD2, GD2 ganglioside
Canonical SMILESCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)O)NC(=O)C)OC4(CC(C(C(O4)C(C(COC5(CC(C(C(O5)C(C(CO)O)O)N)O)C(=O)O)O)O)N)O)C(=O)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
Isomeric SMILESCCCCCCCCCCCCCCCCCC(=O)NC(CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O[C@H]3[C@@H]([C@H]([C@H]([C@H](O3)CO)O)O)NC(=O)C)O[C@@]4(C[C@H]([C@@H]([C@H](O4)C(C(CO[C@@]5(C[C@H]([C@@H]([C@H](O5)C(C(CO)O)O)N)O)C(=O)O)O)O)N)O)C(=O)O)O)O)O)C(/C=C/CCCCCCCCCCCCC)O


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