Methyl a-D-glucopyranoside

a-甲基-D-葡萄糖苷

Methyl alpha-D-glucopyranoside is a white, crystalline compound with a molecular weight of 194.18 g/mol. It is an alpha-anomer and a methylated derivative of D-glucose. Methyl alpha-D-glucopyranoside is widely used in scientific research as a chemical probe for evaluating biological systems. It is a non-toxic and non-metabolizable compound that can mimic the behavior of glucose in cells. Its use in scientific research has expanded to encompass analytical chemistry, biomedical research, and pharmaceutical applications.

Synthesis and Characterization:

Methyl alpha-D-glucopyranoside can be synthesized by the methylation of alpha-D-glucose using methyl iodide and sodium hydride or aluminum hydride. The characterization of methyl alpha-D-glucopyranoside can be performed using various physical and chemical techniques, such as nuclear magnetic resonance (NMR) spectroscopy, mass spectrometry (MS), and infrared (IR) spectroscopy.

Analytical Methods:

Methyl alpha-D-glucopyranoside is commonly used as a standard in analytical chemistry for evaluating the purity and potency of glucose binding proteins, such as lectins or enzymes. The compound can be analyzed using various chromatographic techniques, such as high-performance liquid chromatography (HPLC) and gas chromatography-mass spectrometry (GC-MS).

Biological Properties:

Methyl alpha-D-glucopyranoside is non-toxic to most organisms, including bacteria, fungi, and mammals, due to its inability to be metabolized by the cell. It can be used as a competitive inhibitor of glucose transporters or as a substrate for enzymes that cleave glycosidic bonds. Its effectiveness in these applications depends on the selectivity and affinity of the biological system.

Toxicity and Safety in Scientific Experiments:

Methyl alpha-D-glucopyranoside is safe to handle and use in scientific experiments due to its low toxicity and inertness. It does not pose any significant health or environmental hazards when handled according to standard laboratory safety procedures.

Applications in Scientific Experiments:

Methyl alpha-D-glucopyranoside has many applications in scientific experiments, such as a non-metabolizable glucose analog, a substrate for glycosyltransferases, a specificity control for glucose binding proteins, including lectins and enzymes, and a probe for investigating biological systems. The compound has been used in many different fields of research, such as cancer biology, microbiology, pharmacology, and biochemistry.

Current State of Research:

Current research has focused on the synthesis and characterization of new analogs of methyl alpha-D-glucopyranoside that have improved specificity and affinity for target proteins. These new analogs could lead to more effective inhibitors or probes for studying biological systems. The future of research will likely focus on the further development of these analogs along with their application in various fields of research.

Potential Implications in Various Fields of Research and Industry:

Methyl alpha-D-glucopyranoside and its analogs have the potential to impact various fields of research and contribute to the development of new drugs and therapies. In cancer biology, they could be used as inhibitors of glucose transporters in cancer cells, leading to new treatments for cancer. In microbiology, they could be used to better understand bacterial or viral glucose metabolism. In pharmacology, they could assist in the discovery of new drugs that target glucose metabolism or glucose binding proteins.

Limitations:

One limitation of methyl alpha-D-glucopyranoside is its lack of specificity for glucose binding proteins. The compound can bind to many proteins that have glucose-binding sites, making it less effective as a probe for the study of specific proteins.

Future Directions:

Future research could focus on the development of more specific analogs of methyl alpha-D-glucopyranoside that have higher selectivity for target proteins. Additionally, research could investigate the use of methyl alpha-D-glucopyranoside in targeted drug delivery, as it can bind to glucose transporters and be transported into cells. Finally, more research could be done on the potential uses of methyl alpha-D-glucopyranoside in the food industry and agriculture as a non-caloric sweetener or growth regulator for plants.

Title: a-Methylglucoside

CAS Registry Number: 97-30-3

CAS Name: Methyl-a-D-glucopyranoside

Molecular Formula: C7H14O6

Molecular Weight: 194.18

Percent Composition: C 43.30%, H 7.27%, O 49.44%

Literature References: Prepd by refluxing finely powdered glucose with methanol-HCl: Fischer, Ber. 26, 2405; 27, 2987; 28, 1151 (1895); Helferich, Schäfer, Org. Synth. coll. vol. I, (2nd ed., 1941) 364. Enzymatic synthesis by means of a-glucosidase from yeast: Bourquelot et al., Compt. Rend. 156, 491 (1913). Prepd industrially by reacting glucose with methanol in the presence of a cation exchange material: Chem. Eng. News 33, 4592 (1955). Monograph: G. N. Bollenback, Methyl Glucoside, Preparation, Physical Constants, Derivatives (Academic Press, New York, 1958).

Properties: Orthorhombic bisphenoidal crystals, d430 1.46. mp 168°. bp0.2 200°. [a]D20 +158.9° (p = 10). pKa (25°): 13.71. Soly at 17° in water 63% (w/w); in 80% alcohol 7.3%; in 90% alcohol 1.6%. Practically insol in ether. Soly also reported at 20° as 108 g/100 g H2O and as 5.2 g/100 g methanol.

Melting point: mp 168°

Boiling point: bp0.2 200°

pKa: pKa (25°): 13.71

Optical Rotation: [a]D20 +158.9° (p = 10)

Density: d430 1.46

Use: Manuf reconstituted and upgraded drying oils; tall oil esters and varnishes; fatty acid esters; plasticizers; nonionic surface active agents; fast and hard drying alkyd resins, and so-called plasticizing alkyds. In making glucoside hydroxypropyl ethers for polyurethan foam production.

COA:

Product name: Methyl-alpha-D-glucopyranoside                                                   CAS: 97-30-3

M.F.: C₇H₁₄O₆           M.W.: 194.18       Batch No: 20140302                                  Quantity: 67kg

References:

1. van Rooijen JJA, Voskamp AF, Kamerling JP, Vliegenthart JFG, Glycobiology Vol9, No1, p21-30