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103302-12-1 , Epilactose , 4-O-(b-D-Galactopyranosyl)-D-mannopyranose

103302-12-1 , Epilactose ,
4-O-(b-D-Galactopyranosyl)-D-mannopyranose
C12H22O11 / 342.30
MFCD09953427

Epilactose , 4-O-(b-D-Galactopyranosyl)-D-mannopyranose

The monosaccharide 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate, also known as GM1, is a glycolipid that is essential to mammalian development, specifically in the central and peripheral nervous systems. GM1 is recognized to play significant roles in synaptic plasticity, long-term potentiation, and the regulation of neuronal signaling. This paper aims to provide a comprehensive overview of the chemical, physical, and biological properties of GM1, its synthesis and characterization, analytical methods used, its applications, and its potential implications in various fields of research and industry.

Definition and Background

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate is a type of glycosphingolipid, a class of molecules consisting of a ceramide lipid component covalently attached to a carbohydrate head group. The ceramide is comprised of a long-chain base and one or more fatty acids, and the carbohydrate head group is typically a monosaccharide or oligosaccharide. 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has one galactose sugar unit and one mannose sugar unit.

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate is found in high concentrations in the brain tissue of mammals, where it is essential for synaptic activity and neuronal signaling. Specifically, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate binds to and activates the protein tyrosine kinase receptor TrkA and is involved in the regulation of signal transduction pathways for a range of neurotransmitters, including dopamine, acetylcholine, and serotonin.

Physical and Chemical Properties

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate is a white amorphous solid notable for its high solubility in water, with a solubility of approximately 2 g/L at room temperature. Its molecular weight is approximately 1600 g/mol. 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate is composed of a globotriaosylceramide ceramide moiety attached to an oligosaccharide head group consisting of a galactose and mannose sugar unit.

Synthesis and Characterization

The synthesis of 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate involves the enzymatic addition of a galactose unit to a GM2 ganglioside precursor by the β-galactosyltransferase enzyme. The resulting 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate structure is further modified through the action of several glycosyltransferases to produce additional glycoforms of the molecule, depending on specific cell types.

The main analytical methods used to characterize 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate include high-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS). HPLC separates the different glycoforms of the molecule based on differences in their physical and chemical properties, while NMR and MS provide information on the chemical structure of 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate.

Biological Properties

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been found to play a critical role in mammalian development, particularly in the central and peripheral nervous systems. Specifically, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been implicated in synaptic plasticity, long-term potentiation, and the regulation of neuronal signaling. 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate is also known to bind and activate the TrkA protein tyrosine kinase receptor, which plays a role in regulating the activity of a range of neurotransmitters, including dopamine, acetylcholine, and serotonin.

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been shown to have neuroprotective effects in a range of experimental paradigms, including in animal models of Parkinson's disease, Alzheimer's disease, and stroke. In these models, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been shown to reduce the extent of neuronal damage and improve motor and cognitive function.

Toxicity and Safety in Scientific Experiments

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been extensively studied in animal models and in vitro in various toxicological and safety assays. Overall, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been found to have low toxicity and to be well-tolerated. However, some studies have reported that high doses of 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate can lead to adverse effects, such as diarrhea, vomiting, and weight loss. Nonetheless, these effects are generally mild and transient and have not been observed in clinical trials.

Applications in Scientific Experiments

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has a range of applications in scientific experiments, particularly in neurobiology and neuroscience. 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been used as a tool for studying synaptic plasticity, long-term potentiation, and neuronal signaling. Specifically, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been shown to regulate the activity of a range of neurotransmitters and to enhance neuronal repair and regeneration.

Current State of Research

4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate is an area of active research, particularly in the field of neurobiology and neuroscience. Recent studies have focused on understanding the molecular mechanisms underlying 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate's neuroprotective effects and its utility as a therapeutic agent in neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, and stroke.

Potential Implications in Various Fields of Research and Industry

The potential implications of 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate in various fields of research and industry are vast. In neurobiology and neuroscience, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate holds great promise as a therapeutic agent for the treatment of neurodegenerative diseases such as Parkinson's disease, Alzheimer's disease, and stroke. 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate is also being investigated for its potential in improving the outcome of spinal cord injuries and traumatic brain injuries.

Outside of neurobiology and neuroscience, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has applications in immunology, cell biology, and cancer research. Specifically, 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate has been shown to enhance the activity of natural killer cells and to promote the differentiation and proliferation of various cell types.

Limitations and Future Directions

One limitation of 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate research is the lack of standardization in the synthesis and characterization of the molecule. Currently, there is variability in the techniques used to synthesize 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate and differences in the glycoforms produced. This variability can introduce confounding factors when comparing experimental results across studies.

Future directions in 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate research include the ongoing investigation of the molecular mechanisms underlying 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate's neuroprotective effects, the development of more standardized synthesis and characterization techniques, and the translation of 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate-based therapies to clinical trials. Additionally, more research is needed to determine the potential applications of 4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate outside of neurobiology and neuroscience.

CAS Number103302-12-1
Product Name4-O-(b-D-Galactopyranosyl)-a-D-mannopyranose monohydrate
IUPAC Name(2R,3R,4S,5R,6S)-2-(hydroxymethyl)-6-[(2R,3S,4R,5S,6S)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol;hydrate
Molecular FormulaC12H24O12
Molecular Weight360.31 g/mol
InChIInChI=1S/C12H22O11.H2O/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17;/h3-20H,1-2H2;1H2/t3-,4-,5+,6+,7-,8+,9-,10-,11+,12+;/m1./s1
InChI KeyWSVLPVUVIUVCRA-OCHQEDKVSA-N
SMILESC(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)O)CO)O)O)O)O.O
Canonical SMILESC(C1C(C(C(C(O1)OC2C(OC(C(C2O)O)O)CO)O)O)O)O.O
Isomeric SMILESC([C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@@H]([C@H]([C@H]2O)O)O)CO)O)O)O)O.O


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