α-D-Glucopyranosyl Fluoride

α-D-Glucopyranosyl Fluoride

α-D-Glucopyranosyl Fluoride (CAS No. 2106-10-7) is a specialized glycosylated compound widely used in carbohydrate chemistry and biochemical research. This compound is particularly significant for its application in the synthesis of glycosyl fluorides, which serve as important intermediates in the development of glycosylated drugs and other bioactive molecules.

Chemical Properties

• CAS Number: 2106-10-7
• MDL Number: MFCD34178913
• EINECS: Not available
• Molecular Formula: C6H11FO5
• Molecular Weight: 182.15 g/mol
• Boiling Point: 371.3 ± 42.0 °C at 760 mmHg
• Melting Point: 190-200 °C (decomposes)
• Density: 1.59 g/cm³
• Flash Point: 170.6 °C

Structure and Composition

The structure of α-D-Glucopyranosyl Fluoride consists of a glucopyranoside backbone with a fluorine atom substituting a hydroxyl group at the anomeric position. Key structural features include:

1. Fluorine Substitution: The presence of the fluorine atom enhances the reactivity of the compound, making it a useful building block in glycosylation reactions.
2. Glucopyranoside Backbone: The glucopyranoside structure is essential for biological recognition processes, allowing for interactions with various biomolecules.
3. Hydroxyl Groups: Multiple hydroxyl groups contribute to the solubility and reactivity of the compound, facilitating its use in various chemical reactions.

Applications

α-D-Glucopyranosyl Fluoride is utilized in several applications:

Biochemical Research

1. Glycosylation Reactions: The compound serves as a donor in glycosylation reactions, enabling the synthesis of glycosides and other carbohydrate derivatives.
2. Synthesis of Glycosyl Fluorides: It is used to produce glycosyl fluorides that can act as intermediates in the synthesis of complex carbohydrates and glycoconjugates.

Pharmaceutical Development

1. Drug Design: Its properties make it a candidate for developing glycosylated drugs that require specific targeting mechanisms or enhanced bioactivity.

Enzymatic Assays

1. Substrate for Enzymes: α-D-Glucopyranosyl Fluoride can be employed in assays to measure the activity of glycosidases and other carbohydrate-active enzymes.

Safety and Handling

While specific safety data for α-D-Glucopyranosyl Fluoride are not extensively documented, standard laboratory safety practices should be followed:

1. Personal Protective Equipment (PPE): Use gloves, goggles, and lab coats when handling this compound to avoid skin or eye contact.
2. Ventilation: Work in a well-ventilated area or fume hood to minimize exposure to vapors or dust.
3. Storage Conditions: Store the compound at temperatures between 2 to 8 °C to maintain stability.
4. Disposal Guidelines: Dispose of waste according to local regulations regarding hazardous materials.

Summary

In summary, α-D-Glucopyranosyl Fluoride (CAS No. 2106-10-7) is an essential reagent in carbohydrate chemistry and biochemical research for studying glycosylation processes and synthesizing glycosylated compounds. Its unique structural features enable its use in drug development and enzymatic assays, making it a valuable tool for researchers in the field.

Citations:

1. https://www.chemsrc.com/en/cas/2106-10-7_82262.html
2. https://pubchem.ncbi.nlm.nih.gov/compound/alpha-D-Glucopyranosyl-fluoride
3. https://pubchem.ncbi.nlm.nih.gov/compound/11142654
4. https://www.glpbio.com/sp/945-d-glucopyranosyl-fluoride.html
5. https://m.chemicalbook.com/ProductChemicalPropertiesCB53141093_EN.htm
6. https://www.tcichemicals.com/IN/en/p/T1995
7. https://www.sigmaaldrich.com/US/en/product/astatechinc/ateh03ab3dde?context=bbe
8. https://www.chemicalbook.com/ChemicalProductProperty_EN_CB61397808.htm