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  • 37758-47-7 , Monosialogangloside GM1
37758-47-7 , Monosialogangloside GM1

37758-47-7 , Monosialogangloside GM1

37758-47-7 , Monosialogangloside GM1,
Cas:37758-47-7
C73H131N3O31 / 1546.82

Monosialogangloside GM1,

Monosialoganglioside GM1 (GM1) is a type of ganglioside, which is a type of glycosphingolipid (GSL) that contains sialic acid residues. Gangliosides are present in the outer leaflet of the plasma membrane of mammalian cells, particularly in the nervous system. Monosialoganglioside GM1 is a naturally occurring ganglioside present in high concentrations in the brain and other neural tissues.

Synthesis and Characterization:

Monosialoganglioside GM1 can be isolated from natural sources, such as brain tissue, or synthesized chemically. The chemical synthesis of GM1 involves the stepwise assembly of the oligosaccharide portion on a ceramide backbone. The synthesis can be achieved through various chemical methods, including enzymatic synthesis, chemoenzymatic synthesis, and total synthesis.

Analytical Methods:

Various analytical methods can be used to identify and quantitate Monosialoganglioside GM1, including high-performance liquid chromatography (HPLC), mass spectrometry (MS), capillary electrophoresis (CE), and nuclear magnetic resonance (NMR) spectroscopy.

Biological Properties:

Monosialoganglioside GM1 plays a critical role in various biological processes, particularly in the nervous system, where it is involved in neuronal differentiation, neurite outgrowth, and synaptic plasticity. GM1 has also been shown to have anti-inflammatory, anti-apoptotic, and immunomodulatory effects.

Toxicity and Safety in Scientific Experiments:

Several studies have investigated the toxicity and safety of Monosialoganglioside GM1 in various scientific experiments. In general, GM1 has been found to have a low toxicity profile and to be safe for use in experimental animals and humans.

Applications in Scientific Experiments:

Monosialoganglioside GM1 has numerous applications in scientific experiments, particularly in the field of neuroscience. GM1 can be used as a neurotrophic factor to promote neuronal survival and regeneration, and as a therapeutic agent to treat various neurological disorders, such as Alzheimer's disease, Parkinson's disease, and spinal cord injuries.

Current State of Research:

Numerous studies are ongoing to investigate the potential applications of Monosialoganglioside GM1 in various fields of research, such as neuroscience, immunology, and oncology.

Potential Implications in Various Fields of Research and Industry:

Monosialoganglioside GM1 has the potential to revolutionize various fields of research and industry, particularly in the development of novel therapeutics for neurological disorders and cancer. GM1 also has applications in the field of regenerative medicine, where it can be used to promote tissue regeneration and repair.

Limitations and Future Directions:

Despite its numerous potential applications, Monosialoganglioside GM1 has limitations that need to be addressed in future research. These limitations include its limited availability, high cost, and the need for further studies to investigate its efficacy and safety in humans. Future research directions include the development of more efficient and cost-effective methods for synthesizing and producing GM1, and the investigation of its mechanisms of action and potential applications in various fields of research and industry.

Some future directions could be:

1. Studying the potential use of Monosialoganglioside GM1 as a treatment for autoimmune diseases

2. Investigating the role of Monosialoganglioside GM1 in cancer immunotherapy

3. Developing novel drug delivery systems for Monosialoganglioside GM1

4. Investigating the potential use of Monosialoganglioside GM1 in the treatment of spinal cord injuries

5. Studying the effect of Monosialoganglioside GM1 on cell signaling and gene expression in various cell types

6. Developing synthetic analogs of Monosialoganglioside GM1 with improved efficacy and safety profiles

7. Investigating the potential use of Monosialoganglioside GM1 in wound healing and tissue regeneration.


Title: Gangliosides

Literature References: Animal glycosphingolipids occurring in highest concentration in the central nervous system but widely distributed in other tissues. Primarily located in the outer surface of mammalian cell plasma membranes, they are also found in the synaptic membrane of the central nervous system. More than 60 gangliosides have been characterized. Each consists of a fatty acid (often stearic acid) and an oligosaccharide moiety, both attached to sphingosine. Sialic acid, q.v., is the identifying sugar. The sialic acid residues of gangliosides and those of glycoprotein are the main cause of cell surface negative charge. Gangliosides are also thought to be involved in many different cell functions, e.g. metabolism, growth, malignant transformation. Ganglioside nomenclature: L. Svennerholm, "Ganglioside Metabolism" in Comprehensive Biochemistry vol. 18, M. Florkin, E. H. Stotz, Eds. (Elsevier, Amsterdam, 1970) pp 201-204. Isoln from normal brain and from the brain of patients with Tay-Sachs disease: Klenk, Z. Physiol. Chem. 268, 50 (1941); 273, 76 (1942); Trams, Lauter, Biochim. Biophys. Acta 60, 350 (1962); Svennerholm, Acta Chem. Scand. 17, 239 (1963). Occurrence of different gangliosides: Kuhn, Egge, Angew. Chem. 72, 805 (1960). Chromatographic studies: Kuhn et al., ibid. 73, 580 (1961); Klenk, Gielen, Z. Physiol. Chem. 326, 144 (1961). Structure of ganglioside GI (or GM1): Kuhn, Wiegandt, Ber. 96, 866 (1963). Structure of gangliosides GI and GII (or GD1a): Kuhn, Egge, ibid. 96, 3338 (1963). Structure of gangliosides GII, GIII (or GD1b) and GIV (or GT1b): Kuhn, Wiegandt, Z. Naturforsch. 18b, 541 (1963). Molecular diversity, biological implications of brain and thymus gangliosides: Y. Nogai, M. Iwamori, Mol. Cell. Biochem. 29, 81 (1980). Biosynthesis in tissues: S. Basu et al., Adv. Exp. Med. Biol. 125, 213 (1980). Action as biotransducers of membrane-mediated information: R. O. Brady, P. H. Fishman, Adv. Enzymol. 50, 303 (1979). Reviews: Wiegandt, Angew. Chem. Int. Ed. 7, 87-96 (1968). Collection of articles on structure and function: Adv. Exp. Med. Biol. 125, 1-555 (1980); on structure analysis, function and properties, regeneration and recovery in the nervous system, clinical trials in amyotropic lateral sclerosis and diabetic neuropathy: ibid. 174, 1-649 (1984). Book: Gangliosides in Neurological and Neuromuscular Function, Development, and Repair M. M. Rapport, A. Gorio, Eds. (Raven Press, New York, 1981) 267 pp.

Properties: Gangliosides are colorless crystallizable substances which melt with decompn. Insol in non-polar solvents. Soly in polar solvents increases with the size of the sugar residue and the sialic acid content. Forms micelles in aq soln, having mol wt of about 200,000-250,000. Forms molecular solns in DMF or tetrahydrofuran, having mol wt of 1000-3000.

 

Derivative Type: Ganglioside GM1

CAS Registry Number: 37758-47-7

Additional Names: Siagoside

Trademarks: Sygen (Fidia)

Molecular Formula: C73H131N3O31

Molecular Weight: 1546.82

Percent Composition: C 56.68%, H 8.54%, N 2.72%, O 32.06%

 

Derivative Type: Combination of gangliosides GM1, GD1a, GD1b, and GT1b

Trademarks: Cronassial (Fidia); Gangliovet (Fidia)

 

Therap-Cat: In treatment of peripheral neuropathies.

Therap-Cat-Vet: In treatment of peripheral neuropathies.

CAS Number37758-47-7
Product NameMonosialogangloside GM1
IUPAC Name(2S,4S,5R,6R)-5-acetamido-6-[3-[(2S,3R,4R,5S,6R)-5-[(2S,3R,4R,5R,6R)-3-acetamido-5-hydroxy-6-(hydroxymethyl)-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-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-1,2-dihydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid
Molecular FormulaC73H130N3O31
Molecular Weight1546.82 g/mol
InChIInChI=1S/C73H131N3O31/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(86)76-44(45(83)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)40-99-69-61(93)59(91)63(50(38-79)102-69)104-71-62(94)67(98-41-47(85)55(87)66-53(74-42(3)81)46(84)35-73(97,107-66)72(95)96)64(51(39-80)103-71)105-68-54(75-43(4)82)65(57(89)49(37-78)100-68)106-70-60(92)58(90)56(88)48(36-77)101-70/h31,33,44-51,53-71,77-80,83-85,87-94,97H,5-30,32,34-41H2,1-4H3,(H,74,81)(H,75,82)(H,76,86)(H,95,96)/b33-31+/t44?,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-,71-,73-/m0/s1
InChI KeyQPJBWNIQKHGLAU-IQZHVAEDSA-M
SMILESCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)OC4C(C(C(C(O4)CO)O)O)O)NC(=O)C)OCC(C(C5C(C(CC(O5)(C(=O)O)O)O)NC(=O)C)O)O)O)O)O)C(C=CCCCCCCCCCCCCC)O
SynonymsGM1;Monosialoganglioside GM1
Canonical SMILESCCCCCCCCCCCCCCCCCC(=O)NC(COC1C(C(C(C(O1)CO)OC2C(C(C(C(O2)CO)OC3C(C(C(C(O3)CO)O)OC4C(C(C(C(O4)CO)O)O)O)NC(=O)C)OCC(C(C5C(C(CC(O5)(C(=O)O)O)O)NC(=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[C@H]4[C@@H]([C@H]([C@H]([C@H](O4)CO)O)O)O)NC(=O)C)OCC(C([C@H]5[C@@H]([C@H](C[C@](O5)(C(=O)O)O)O)NC(=O)C)O)O)O)O)O)C(/C=C/CCCCCCCCCCCCC)O


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