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L-Fucose

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CAS:2438-80-4
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L-Fucose Basic information
Product Name:L-Fucose
Synonyms:6-DESOXY-L-GALACTOSE;L-(-)-RHODEOSE;L-FUCOSE;FUCOSE, L-;6-deoxy-l-galactos;L-FUCOSE, 99.6% MIN., TLC;6-methyloxane-2,3,4,5-tetrol;L-(-)-FUCOSE:6-DEOXY-L-GALACTOSE
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;Glycon Biochem
Mol File:2438-80-4.mol
L-Fucose Structure
L-Fucose Chemical Properties
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
pka12.50±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.
InChIKeySHZGCJCMOBCMKK-DLABPRKASA-N
LogP-0.340 (est)
CAS DataBase Reference2438-80-4(CAS DataBase Reference)
EPA Substance Registry SystemL-Galactose, 6-deoxy- (2438-80-4)
Safety Information
Safety Statements 24/25
WGK Germany 3
3-10
TSCA Yes
HS Code 29400090
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
L-Fucose Usage And Synthesis
DescriptionL-(−)-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 PropertiesWhite crystalline powder, soluble in methanol, ethanol, DMSO and other organic solvents.
Chemical Propertiesl-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].
OccurrenceL-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.
UsesL-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.
DefinitionChEBI: 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.
ReactionsL-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 Functionsl-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 ActivityL-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.
L-Fucose Preparation Products And Raw materials
Preparation Products2-Chloro-4-nitrophenyl-alpha-L-fucopyranoside-->D-(+)-GALACTOSE-->1,2,3,4-Tetra-O-benzoyl-L-fucopyranose
Tag:L-Fucose(2438-80-4) Related Product Information
MUCIC ACID D-GALACTURONIC ACID TRIGALACTURONIC ACID METHYL 2,3,4-TRI-O-ACETYL-BETA-D-THIOGALACTOPYRANOSIDURONIC ACID METHYL ESTER L-GALACTONO-1,4-LACTONE L-Fucose ALPHA-D-GALACTURONIC ACID HYDRATE Isometheptene mucate 6-DEOXY-L-GALACTITOL 4-NITROPHENYL-BETA-D-FUCOSE L-(-)-FUCOSE,L-FUCOSE 4-NITROPHENYL-BETA-D-FUCOSE FUCOSE, D-(+)-,D-(+)-FUCOSE,D-FUCOSE P-NITROPHENYL BETA-D-GALACTOPYRANOSIDURONIC ACID ALPHA-L-MANNOHEPTOSE ALPHA-D-GALACTURONIC ACID 1-PHOSPHATE LITHIUM SALT DIGALACTURONIC ACID L-[3-13C]FUCOSE

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