Cellobiosyl fluoride 

Cellobiosyl fluoride is a chemically synthesized glycosyl fluoride derivative of cellobiose, a disaccharide composed of two glucose units linked by a β(1→4) glycosidic bond. In this compound, the reducing end hydroxyl group of cellobiose is replaced by a fluorine atom, forming a stable glycosyl fluoride. Cellobiosyl fluorides play an essential role as glycosyl donors in carbohydrate synthesis, offering controlled reactivity and stereoselectivity in glycosylation reactions. The fluorine substitution enhances the glycosidic bond’s stability toward enzymatic hydrolysis while maintaining reactivity in catalytic processes, making it valuable for synthesizing complex oligosaccharides and glycoconjugates. Typically appearing as a white crystalline solid, cellobiosyl fluoride is supplied with high purity and rigorous quality assurance. It is widely used in synthetic glycobiology, enzymatic mechanism studies, glycomimetic design, and facilitating drug discovery in carbohydrate-related therapeutics. The compound is stored under refrigerated conditions and has a stable shelf life suitable for long-term research applications.​

IUPAC Name

• (1→4)-β-D-glucopyranosyl 1-fluoride​

Appearance

• White crystalline powder​

Source

• Chemically synthesized from cellobiose via selective fluorination of the reducing end hydroxyl group under controlled laboratory conditions​

Molecular Weight and Structure

• Molecular Formula: C12H19FO10
• Molecular Weight: Approximately 326.27 g/mol​
• Structure: Cellobiose disaccharide with 1-fluoride substitution at the reducing glucose unit
• Features β(1→4) glycosidic linkage between glucose monomers and fluorine replacing the anomeric hydroxyl​
• SMILES: C1(C(C(C(C(O1)OC2C(C(C(C(O2)F)O)O)O)O)O)O)F​

Sugar Specificity

• Disaccharide glycosyl fluoride of cellobiose exhibiting β(1→4) glucosyl linkage specificity
• Reactivity tailored for glycosyl donor activity in carbohydrate synthesis​

Biological Activity

• Functions primarily as a synthetic intermediate rather than possessing intrinsic bioactivity
• Utilized as a probe in enzymatic mechanism studies of glucosyltransferases and hydrolases
• Supports development of glycomimetics and biochemical tools​

Purity and Microbial Contamination

• Typically supplied with ≥95% purity confirmed by chromatographic and spectral analysis
• Production involves stringent purification and sterile handling to limit microbial contamination​

Identity and Quality Control

• Quality verified by NMR spectroscopy (1H, 13C, 19F), mass spectrometry, HPLC purity profiles
• Full documentation including Certificate of Analysis and Safety Data Sheets available
• Melting point and spectral data provided for compound verification​

Shelf Life and Storage

• Store at 2–8 °C, protected from moisture and light
• Stability spans over 1 year with appropriate storage conditions
• Containers must be tightly sealed to maintain compound integrity​

Application

• Key glycosyl donor in the chemical synthesis of oligosaccharides and glycoconjugates
• Enables regio- and stereoselective glycosylation reactions
• Used in mechanistic studies of enzymatic glycosylation and glycosidic bond formation
• Supports drug discovery, molecular probe development, and diagnostic research in glycoscience​

Key Characteristics

• Fluorinated glycosyl donor derived from cellobiose
• Molecular weight approx. 326.27 g/mol
• White crystalline solid with high purity (≥95%)
• Stable and analytically verified for research use
• Critical reagent in carbohydrate synthesis and glycoscience
• Supplied with rigorous quality control and identity verification
• Facilitates advanced synthetic and enzymology studies in glycobiology

Citation

• ChemicalBook glycosyl fluoride data​
• Sigma-Aldrich related glycosyl fluorides​
• PMC enzymatic glycosylation studies​
• Patents on cellobiosyl fluorides and synthesis​
• Synthose carbohydrate reagent catalog​
• PubChem fluorosugar intermediates​
• ScienceDirect glycosylation chemistry articles​
• MedChemExpress fluorinated sugar intermediates​
• Glentham Life Sciences product details​
• BOC Sciences related carbohydrate reagents​