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HomeProduct name listL-Fucose

L-Fucose

Synonym(s):L-(−)-Fucose;6-Deoxy-L-galactose

  • CAS NO.:2438-80-4
  • Empirical Formula: C6H12O5
  • Molecular Weight: 164.16
  • MDL number: MFCD00135607
  • EINECS: 219-452-7
  • SAFETY DATA SHEET (SDS)
  • Update Date: 2024-11-12 16:52:33
L-Fucose Structural

What is L-Fucose?

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.

The Uses of L-Fucose

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.

What are the applications of Application

L-(?)-Fucose is a glycan modifying carbohydrate

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.

Properties of L-Fucose

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.
CAS DataBase Reference 2438-80-4(CAS DataBase Reference)
EPA Substance Registry System L-Galactose, 6-deoxy- (2438-80-4)

Safety information for L-Fucose

Signal word Warning
Pictogram(s)
ghs
Exclamation Mark
Irritant
GHS07
GHS Hazard Statements H302:Acute toxicity,oral
H315:Skin corrosion/irritation
H319:Serious eye damage/eye irritation
H335:Specific target organ toxicity, single exposure;Respiratory tract irritation
Precautionary Statement Codes P261:Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Computed Descriptors for L-Fucose

InChIKey SHZGCJCMOBCMKK-DLABPRKASA-N

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