D-Fucose is a naturally occurring six-carbon deoxy sugar, specifically a 6-deoxyhexose, where the hydroxyl group at the 6th carbon of D-galactose is replaced by hydrogen. It exists as a white crystalline powder and plays important roles in biological systems, particularly in mammalian and plant glycans. D-Fucose is a critical component of N-linked glycans on cell surfaces and participates in various cellular recognition and signaling processes. It is a building block of fucoidan, a sulfated polysaccharide found in brown algae with diverse biological activities, including anti-inflammatory and anticancer properties. This sugar is used extensively in biochemical research for glycan analysis, cell adhesion studies, and development of glycomimetics. Synthetic D-fucose is available with high purity for research in glycobiology, immunology, and medicine. It contributes to understanding carbohydrate-mediated biological interactions and therapeutic development.
IUPAC Name
- (2R,3S,4S,5R)-2,3,4,5-tetrahydroxyhexanal
- Synonyms: 6-deoxy-D-galactose, (+)-Fucose, Rhodeose
Appearance
- White crystalline powder
Source
- Naturally found in mammals and plants; commercially synthesized for research
Molecular Weight and Structure
- Molecular Formula: C6H12O5
- Molecular Weight: 164.16 g/mol
- Structure: Six-carbon sugar with a missing hydroxyl at C6 (deoxy), with aldehyde group at C1
- SMILES: CC@@HC@HC@HC@@HC=O
Sugar Specificity
- A 6-deoxyhexose sugar, specific to fucose metabolic pathways
- Present on N-linked glycans and polysaccharides such as fucoidan
Biological Activity
- Key role in cell-cell recognition, adhesion, and immune response
- Modifies glycoproteins affecting signaling pathways and developmental processes
- Implicated in selectin-mediated leukocyte trafficking and cancer biology
Purity and Microbial Contamination
- Purity typically ≥97-99% by HPLC/GC for research grade
- Microbial contamination negligible in chemical-grade material
Identity and Quality Control
- Verified by NMR, GC, HPLC, optical rotation
- Melting point: approx. 144-145 °C
- Specific rotation: +72 to +76 degrees (water)
Shelf Life and Storage
- Store at 2–8 °C to maintain stability
- Stable for 3-5 years under recommended conditions
- Protect from moisture and light
Application
- Used in glycobiology to study glycan structures and functions
- Research reagent in biochemistry, immunology, and cell biology
- Building block for synthesis of fucoidan and other sulfated polysaccharides
- Applied in development of glycomimetics and therapeutic agents
Key Characteristics
- Natural 6-deoxyhexose sugar involved in cell surface glycosylation
- CAS number: 3615-37-0
- White crystalline powder, molecular weight 164.16 g/mol
- High purity, verified by multiple analytical techniques
- Crucial for study of immune cell adhesion and cancer biology
- Stable with recommended refrigerated storage
- Widely used in glycobiology, pharmaceutical research, and biochemistry
Citation
- Sigma-Aldrich D-(+)-Fucose product info
- TCI Chemicals purity and storage
- PubChem molecular data
- Glentham chemical catalog
- PharmaAffiliates CAS and chemical data
- ChemicalBook description
- GoldBio α-D-Fucose overview
- PMC article on fucose biology
- SRL Chemicals storage and shelf life
- LGC Standards D-Fucose
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