Summary
L-fucose (CAS No. 2438-80-4) is a natural sugar, usually derived from brown algae and human breast milk, and also found in certain human organs, such as skin and nervous system. Fucose in nature is often in the L configuration and exists in seaweed in the form of polysaccharides such as fucoidan and fucoidan. D-configuration fucose is only a rare sugar and is found in some glycoglycerides.
L-fucose is a natural sugar commonly derived from brown algae and human breast milk. It is naturally present in certain human organs, including the skin and nervous system. In nature, fucose is often found in the L configuration and exists in seaweed in the form of polysaccharides such as fucoidan.
Chemical Properties
Alias: 6-Deoxy-L-galactose; 6-Deoxy-L-galactose
Molecular Formula: C6H12O5
Molecular Weight: 164.16
Beilstein: 1723321
EC Number: 219-452-7
MDL Number: MFCD00135607
Appearance: Powder
Melting Point: 150-153 ℃ (literature value)
Solubility: 50 mg/mL in water
Biological Effects:
An article published in Nature (01 October 2014; doi: 10.1038/nature 13823) highlights that L-fucose has metabolic effects on intestinal bacteria. In sick mice, L-fucose is produced in the intestines to provide nutrition for the microbiota, contributing to maintaining a healthy microbial balance.
Structural Features:
Different from other six-carbon sugars, fucose has two distinctive structural features: 1) no hydroxyl group on carbon 6 (C-6), and 2) L-configuration. In fucose-containing sugar chain structures, the fucose chain can act as a terminal modification or serve as an attachment point for the binding of other sugars. Fucose is metabolized by L-fucosidase. Elevated levels of free L-fucose in serum and urine are considered markers for conditions such as cancer, cirrhosis, alcoholic liver disease, and gastric ulcer.
Medical Application
Elevated serum fucose levels reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes, and cardiovascular disease.
Feeding rats with high-content L-fucose diets can induce neuropathy similar to that seen in diabetic patients.
Biotechnological Application
Improve Protein Stability and Solubility: L-fucose, as a non-reducing sugar, can undergo glycosylation reactions with proteins, enhancing protein stability and preventing degradation.
Addition of L-fucose to protein preparations aids in stability during transportation and storage.
Increases the solubility of proteins, improving the dissolution rate of injectable preparations.
Reduce Immunogenicity: L-fucose can cover antigenic epitopes on certain proteins, thereby reducing immunogenicity and minimizing immune responses.
Commonly added to certain protein vaccines.
Food Industry Applications
In the food field, L-fucose exhibits promising application prospects. Studies have confirmed its impact on the balance of intestinal flora. During illness, the intestines produce L-fucose to support the health and balance of the flora and microorganisms. Consequently, adding L-fucose to food is beneficial for gut health.