L-Fucose Property

Melting point:

150-153 °C(lit.)

Boiling point:

211.61°C (rough estimate)

alpha 

-73～-77°(D/20℃)(c=4,H2O,24hr)

Density 

1.1738 (rough estimate)

refractive index 

-75.5 ° (C=10, H2O)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

solubility 

H₂O: 0.1 g/mL, clear, colorless

form 

Powder

pka

12.50±0.20(Predicted)

color 

Beige to light brown to purple-grayish

Water Solubility 

Soluble in water.

Sensitive 

Hygroscopic

Merck 

14,4279

BRN 

1723321

Stability:

Stable. Incompatible with strong oxidizing agents.

InChIKey

SHZGCJCMOBCMKK-DLABPRKASA-N

LogP

-0.340 (est)

CAS DataBase Reference

2438-80-4(CAS DataBase Reference)

EPA Substance Registry System

L-Galactose, 6-deoxy- (2438-80-4)

Safety

Safety Statements 

24/25

WGK Germany 

3

F 

3-10

TSCA 

Yes

HS Code 

29400090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

L-Fucose Chemical Properties,Usage,Production

Description

L-(−)-Fucose is a deoxyhexose monosaccharide found on N- and O-linked glycans and glycolipids of a wide variety of organisms. It can exist as a terminal modification of glycan structures or serve as a point of attachment for adding other sugars. In humans, L-(−)-fucose plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

Chemical Properties

White crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents.

Chemical Properties

l-fucose is a six-carbon sugar also known as 6-deoxy-l-galactose. Its molecular formula is C6H12O5 and its melting point is 150.0–153.0 °C. It is a white crystalline powder that easily absorbs moisture, and its hydrophilicity is weaker than that of other monosaccharides. l-fucose is the main form of fucose found in nature and is also the only levorotatory sugar used by mammals, while d-fucose is found only in some glycosides[1].

Occurrence

L-Fucose exists in nature in various biological niches. A major natural source of L-fucose is the brown algal polysaccharide fucoidan. It is also present in the polysaccharides of tragacanth, potatoes, kiwi, soybeans, varieties of wing peas, canola and other plants.L-Fucose is a minor component in plant cell wall polysaccharides, specifically rhamnogalacturonan, xyloglucan and also arabinogalactan proteins that are involved in plant cell elongation.

Uses

L-Fucose was isolated from seaweed. It finds application in cosmetics, pharmaceuticals and dietary supplements. It is used in the determination of antigen in A and B blood group. It is also used in the selection-mediated leukocyte-endothelial adhesion and host-microbe interactions. L-Fucose is also used in anti aging creams as well as to promote the accelerated healing of wounds and to reduce allergy.

Definition

ChEBI: L-fucopyranose is the pyranose form of L-fucose. It has a role as an Escherichia coli metabolite and a mouse metabolite. It is a L-fucose and a fucopyranose.

Reactions

L-Fucose is oxidised by the enzyme L-fucose dehydrogenase in the presence of nicotinamide-adenine dinucleotide phosphate (NADP+) to L-fucono-1,5-lactone with the formation of reduced nicotinamideadenine dinucleotide phosphate (NADPH) (1).
(L-fucose dehydrogenase) (1)
L-Fucose + NADP+ --> L-fucono-1,5-lactone + NADPH + H+
The amount of NADPH formed in this reaction is stoichiometric with the amount of L-fucose. It is the NADPH which is measured by the increase in absorbance at 340 nm.

Biological Functions

l-fucose has many biological functions like the antitumor effect and relieving intestinal disease, and exhibits potential as an emulsifier in the food industry. It can be used as a functional food and one of the components of bacteriostatic agents. Moreover, it also has an anti-aging function[1].

Biological Activity

L-Fucose (6-Deoxy-L-galactose) is used in studies of fucoidan polysaccharides containing glycans. It is studied as a glycan modifying carbohydrate that generates antigenic sites recognized by IgE antibodies. It is used as a substrate to identify, differentiate, and characterize enzymes such as fucosidase(s),l-fucose isomerase(s), and L-fucose dehydrogenase(s). It may be used to study organelles, and bacterial microcompartments, involved in the degradation of plant and algal cell wall sugars. L-Fucose may also be used as a reference compound in rare sugar identification and analysis.

References

[1] Yan Wang . “Research progress on the functions, preparation and detection methods of l-fucose.” Food Chemistry 433 (2023): Article 137393.