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L-Fucose

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L-Fucose Basic information

Product Name:
L-Fucose
Synonyms:
  • 6-DEOXY-BETA-GALACTOSE
  • 6-DEOXY-L-GALACTOSE
  • 6-DESOXY-L-GALACTOSE
  • L-(-)-RHODEOSE
  • L-(-)-FUCOSE
  • L-FUCOSE
  • FUCOSE, L-
  • 6-deoxy-l-galactos
CAS:
2438-80-4
MF:
C6H12O5
MW:
164.16
EINECS:
219-452-7
Product Categories:
  • 13C & 2H Sugars
  • Biochemistry
  • Deoxysugars
  • Fucose
  • Sugars
  • Dextrins、Sugar & Carbohydrates
  • Carbohydrates & Derivatives
Mol File:
2438-80-4.mol
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L-Fucose Chemical Properties

Melting point:
150-153 °C(lit.)
alpha 
-73~-77°(D/20℃)(c=4,H2O,24hr)
Boiling point:
211.61°C (rough estimate)
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
pka
12.50±0.20(Predicted)
form 
Powder
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
CAS DataBase Reference
2438-80-4(CAS DataBase Reference)
EPA Substance Registry System
L-Galactose, 6-deoxy- (2438-80-4)
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Safety Information

Safety Statements 
24/25
WGK Germany 
3
3-10
TSCA 
Yes
HS Code 
29400090

MSDS

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L-Fucose Usage And Synthesis

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.

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 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.

L-Fucose Preparation Products And Raw materials

Preparation Products

L-FucoseSupplier

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