2438-80-4

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 NO: 2438-80-4
• Molecular Formula: C6H12O5
• Molecular Weight: 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
• Article Data: 71

Chemical Properties

• Melting Point: 150-153 °C(lit.)
• Boiling Point: 211.61°C (rough estimate)
• Flash Point: 209.3 °C
• Appearance: Beige to light brown to purple-grayish/Powder
• Density: 1.1738 (rough estimate)
• Vapor Pressure: 5E-08mmHg at 25°C
• Refractive Index: -75.5 ° (C=10, H2O)
• Storage Temp.: -20°C Freezer
• Solubility: H2O: 0.1 g/mL, clear, colorless
• PKA: 12.50±0.20(Predicted)
• Water Solubility: Soluble in water.
• Sensitive: Hygroscopic
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,4279
• BRN: 1723321
• CAS DataBase Reference: L-FUCOSE(CAS DataBase Reference)
• NIST Chemistry Reference: L-FUCOSE(2438-80-4)
• EPA Substance Registry System: L-FUCOSE(2438-80-4)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 2438-80-4(Hazardous Substances Data)

Usage

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.

InChI:InChI=1/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4+,5+,6-/m0/s1

Upstream product

• 7647-01-0 hydrogenchloride 
• 41263-94-9 2′-fucosyllactose 
• 79-06-1 2-propenamide 
• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 7664-93-9 sulfuric acid 
• 106293-98-5 6-deoxy-D-mannono-1,4-lactone 
• 1051388-66-9 (1β,3β,5β,25S)-spirostan-1,3-diol 1-[α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside] 
• 1166398-39-5 8,3'-dihydroxy-3,7,4'-trimethoxy-6-O-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside flavone 
• 1198083-03-2 3α,11α,30-trihydroxylup-23-al-20(29)-en-28-oic acid 28-O-[α-L-rhamnopyranosyl-(1->4)-β-D-glucopyranosyl-(1->6)-β-D-glucopyranosyl] ester 
• 64-19-7 acetic acid 
• 24286-28-0 (3S,4S,5R)-dihydro-3,4-dihydroxy-5-((1'S)-1'-hydroxyethyl)furan-2(3H)-one 
• 84012-04-4 α-L-Fuc-(1-3)-β-D-GalNAc-(1-3)-β-D-Gal-(1-4)-β-D-Gal-(1-3)-D-GalNAc-ol 
• 10231-84-2 (4-nitro-phenyl)-α-L-fucopyranoside 

Downstream Products

• 3616-21-5 L-fuculose 
• 14687-15-1 methyl L-fucopyranoside 
• 1128-40-1 methyl β-L-fucopyranoside 
• 634-74-2 D,L-rhamnose 
• 6422-34-0 L-idomethylonic acid 
• 2079-46-1 arabino-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 620-02-0 5-Methylfurfural 
• 13074-06-1 L-fucitol 
• 26372-13-4 L-fuconic acid 
• 6035-60-5 L-fucose oxime 
• 488-31-3 (2S,4S)-xylaric acid 
• 136572-16-2 1,2:3,4-di-O-isopropylidene-L-fucopyranose 
• 51607-21-7 6-deoxy-D-altritol 
• 20031-16-7 6-deoxy-D-gulono-1,4-lactone 

Relevant articles and documents

Composition, structural characteristics, and antitumor properties of polysaccharides from the brown algae Dictyopteris polypodioides and Sargassum sp.

The polysaccharide compositions of the brown algae Dictyopteris polypodioides and Sargassum sp. from the Mediterranean Sea were determined. The principal polysaccharide of the studied algae (about 12% of the dry alga weight) was alginic acid. The content of water-soluble polysaccharides was low. The amount of fucoidan was less than 1% of the dry alga weight; of neutral polysaccharides, less than 0.25%. The monosaccharide compositions of fucoidans and neutral polysaccharides were investigated. Experiments on soft agar-agar models showed that fucoidans from D. polypodioides and Sargassum sp. exhibited antitumor activity against RPMI-7951 human melanoma cells.

Two new compounds from the fruits of Buddleja lindleyana with neuroprotective effect

Two new triterpenoid glycosides, mimengosides H (1) and I (2), were isolated from the fruits of Buddleja lindleyana Fort. Their structures were determined by extensive spectroscopic methods. Neuroprotective effects of these isolates against 1-methyl-4- phenylpyridinium ion-induced neurotoxicity in PC12 cells were evaluated. Pretreatment with compound 1 had potential protective effect in a concentration range from 0.1 to 1μmol l-1.

Biological activities of fucose-containing polysaccharide ascophyllan isolated from the brown alga Ascophyllum nodosum

A fucose-containing, sulfated polysaccharide ascophyllan was isolated from the brown alga Ascophyllum nodosum. Composition analysis demonstrated that ascophyllan mainly contains uronic acid, xylose, fucose, and sulfate half ester in approximately equimole

Two new flavonol glycosides from the leaves of Elaeagnus pungens

The leaves of Elaeagnus pungens were extracted with 70% ethanol and successively purified by column chromatography. Seven constituents were obtained and characterized, all of which belong to the class of flavonol glycosides. Their structures were elucidat

Structure and gene cluster of the O-antigen of Escherichia coli O41

The acidic O-polysaccharide (O-antigen) of Escherichia coli O41 was studied by sugar analysis along with 1D and 2D 1H and 13C NMR spectroscopy, and the following structure of the branched hexasaccharide repeating unit was established: This structure is unique among the known structures of bacterial polysaccharides. The O-antigen gene cluster of E. coli O41 was sequenced. The gene functions were tentatively assigned by a comparison with sequences in the available databases and found to be in full agreement with the E. coli O41 O-polysaccharide structure.

Design of Artificial Glycosidases: Metallopeptides that Remove H Antigen from Human Erythrocytes

Catalysts that promote carbohydrate degradation have a wide range of potential applications, but the use of either enzyme glycosidases or small-molecule catalysts in biological systems raises significant challenges. Herein, we demonstrate a novel strategy for the design of synthetic agents that mimic natural glycosidases and address current problems for biological use. This strategy is illustrated by application to the development of potential blood substitutes for the rare Bombay blood type that is characterized by a deficiency of H2 antigen. Metallopeptides with 16 to 20 amino acids were constructed as artificial fucosidases that exhibit selective carbohydrate cleavage reactivity toward l-fucose over d-glucose. Selective fucose cleavage from the H2-antigen saccharide enables efficient removal of H2 antigen from erythrocytes and thereby accomplishes the conversion of regular human type-O blood into a potential blood substitute for the rare Bombay blood type.

Structure characterization of the mannofucogalactan isolated from fruit bodies of Quinine conk Fomitopsis officinalis

The mannofucogalactan as a major component of water extract was obtained from fruit bodies of Fomitopsis officinalis by extraction with boiling water followed by deproteination, decoloration, and purification using anion-exchange chromatography and size exclusion chromatography. Its structure was characterized using the data of monosaccharide composition, methylation analysis, one- and two-dimensional NMR spectroscopy. The studied polysaccharide was a branched mannofucogalactan with a backbone composed of partially 3-O-methylated 1,6-O-linked α-D-galactopyranosyl residues. Almost every second residue in the backbone was substituted at O-2 by 3-O-α-D-mannopyranosyl-α-L-fucopyranosyl and β-D-galactopyranosyl residues. The non-reducing terminal α-L-fucopyranosyl units, which were identified by GC–MS analyses, appeared to be the part of mannofucogalactan side chains also.

Steroidal saponin from Polygonatum verticillatum

New steroidal glycoside 1 was isolated by fractionation of total extracted compounds from rhizomes of Polygonatum verticillatum (Convallariaceae). Chemical transformations, physical constants, and spectral data characterized its structure as (25S)-spirost

A novel low-molecular-mass pumpkin polysaccharide: Structural characterization, antioxidant activity, and hypoglycemic potential

The novel natural low-molecular-mass polysaccharide (SLWPP-3) from pumpkin (Cucurbia moschata) was separated from the waste supernatant after macromolecular polysaccharide production and purified using a DEAE cellulose-52 column and gel-filtration chromatography. Chemical and instrumental studies revealed that SLWPP-3 with a molecular mass of 3.5 kDa was composed of rhamnose, glucose, arabinose, galactose and uronic acid with a weight ratio of 1: 1: 4: 6: 15, and primarily contained →3,6)-β-D-Galp-(1→, →4)-α-GalpA-(1→(OMe), →4)-α-GalpA-(1→, →2,4)-α-D-Rhap-(1→, →3)-β-D-Galp-(1→, →4)-α-D-Glcp, and →4)-β-D-Galp residues in the backbone. The branch chain passes were connected to the main chain through the O-4 atom of glucose and O-3 atom of arabinose. Physiologically, the ability of SLWPP-3 to inhibit carbohydrate-digesting enzymes and DPPH and ABTS radicals, as well as protect pancreatic β cells from oxidative damage by decreasing MDA levels and increasing SOD activities, was confirmed. The findings elucidated the structural types of pumpkin polysaccharides and revealed a potential adjuvant natural product with hypoglycemic effects.

Antiangiogenic phenylpropanoid glycosides from Gynura cusimbua

A new phenylpropanoid glycoside, named α-L-rhamnopyranosyl-(1?2)-β-D-[4″-(8E)-7-(3,4-dihydroxyphenyl)-8-propenoate, 1″-O-(7S)-7-(3,4-dihydroxyphenyl)-7-methoxy-ethyl]-glucopyranoside (1), together with nine known compounds (2–10) were isolated from the active fraction (n-Butanol fraction) of Gynura cusimbua for the first time. The known compounds (2–10) were identified as phenylpropanoid glycosides on the basis of extensive spectral data and references. The antiangiogenic activities of compounds (1–10) were evaluated by MTT assay on HUVECs and wild-type zebrafish in vivo model assay. As a result, compounds 1, 6, 7, 8 and 10 exhibited certain antiangiogenic activities.