Methyl β-D-glucopyranoside

Definition

Methyl β-D-glucopyranoside is a monosaccharide derivative formed by the condensation of glucose with methanol. It is a common model compound used to study the reactions and properties of monosaccharides, as outlined in the topic 25.6 Reactions of Monosaccharides.

5 Must Know Facts For Your Next Test

1. Methyl β-D-glucopyranoside is a stable, crystalline compound that serves as a model for studying the reactivity of the pyranose ring structure of glucose.
2. The methyl group is attached to the anomeric carbon (C-1) of the glucose molecule, forming a glycosidic bond in the beta configuration.
3. As a derivative of glucose, methyl β-D-glucopyranoside retains the key functional groups and stereochemistry of the parent monosaccharide.
4. Reactions of methyl β-D-glucopyranoside, such as oxidation, reduction, and substitution, provide insights into the general reactivity of monosaccharides.
5. Methyl β-D-glucopyranoside is commonly used as a standard in analytical techniques like NMR spectroscopy to characterize the structure and stereochemistry of carbohydrates.

Review Questions

• Explain the significance of the methyl group and the beta configuration in the structure of methyl β-D-glucopyranoside.
  • The methyl group in methyl β-D-glucopyranoside is attached to the anomeric carbon (C-1) of the glucose molecule, forming a glycosidic bond. The beta configuration of this bond means that the methyl group is positioned on the opposite side of the pyranose ring compared to the hydroxyl groups. This structural feature makes methyl β-D-glucopyranoside a useful model compound for studying the reactivity and stereochemistry of monosaccharides, as the methyl group provides a stable, non-reducing end that can be easily modified and analyzed.
• Describe how the reactions of methyl β-D-glucopyranoside can provide insights into the general reactivity of monosaccharides.
  • Reactions of methyl β-D-glucopyranoside, such as oxidation, reduction, and substitution, can be used to investigate the reactivity of the pyranose ring structure and the various functional groups present in monosaccharides like glucose. By studying how methyl β-D-glucopyranoside undergoes these transformations, researchers can gain a better understanding of the general reactivity and behavior of monosaccharides, which is crucial for elucidating the mechanisms and applications of carbohydrate chemistry as outlined in topic 25.6 Reactions of Monosaccharides.
• Evaluate the use of methyl β-D-glucopyranoside as a standard in analytical techniques like NMR spectroscopy for the characterization of carbohydrates.
  • Methyl β-D-glucopyranoside is widely used as a standard compound in analytical techniques such as nuclear magnetic resonance (NMR) spectroscopy to characterize the structure and stereochemistry of carbohydrates. Its well-defined structure, with the methyl group providing a stable, non-reducing end, makes it an ideal reference compound. By comparing the NMR signals of unknown carbohydrate samples to those of methyl β-D-glucopyranoside, researchers can accurately identify the anomeric configuration, ring size, and the presence of specific functional groups, which is crucial for elucidating the structure and properties of monosaccharides as outlined in topic 25.6 Reactions of Monosaccharides.

Related terms

Monosaccharide:

The simplest form of carbohydrate that cannot be hydrolyzed into smaller sugar units.

Glycosidic Bond:

The covalent bond formed between a sugar and another molecule, such as an alcohol, creating a glycoside.

Pyranose:

A six-membered ring structure adopted by monosaccharides like glucose, where the ring contains five carbon atoms and one oxygen atom.