F2252
L-(−)-Fucose
≥98% (GC)
Synonym(s):
6-Deoxy-L-galactose
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All Photos(5)
About This Item
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
Beilstein:
1723321
EC Number:
MDL number:
UNSPSC Code:
12352201
PubChem Substance ID:
NACRES:
NA.25
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Quality Level
Assay
≥98% (GC)
form
powder
technique(s)
gas chromatography (GC): suitable
color
white
mp
150-153 °C (lit.)
solubility
H2O: soluble 50 mg/mL, clear to very slightly hazy
SMILES string
C[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)C=O
InChI
1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4+,5+,6-/m0/s1
InChI key
PNNNRSAQSRJVSB-KCDKBNATSA-N
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General description
L-Fucose, a natural monosaccharide found in mammals, is an important component of several N- and O-linked glycans and glycolipids.
Application
L-(−)-Fucose has been used:
- as the non-haptenic sugar in lectin bead-binding assay to study its effects on the binding of immobilized lectins like peanut agglutinin (PNA) and Dolichos biflorus agglutinin (DBA)
- as an internal standard to dilute the enzymatic hydrolysates for analytical methods
- in the synthesis of fucosyl thioglycoside
Biochem/physiol Actions
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. L-Fucose 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 is broadly used as a food additive. It possesses anti-inflammatory effects. It can inhibit the cutaneous immune reaction and alveolar macrophage priming. L-fucose can also suppress tumor growth and tumorigenesis.
Other Notes
To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.
Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
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Jing-Jing Liu et al.
Biotechnology and bioengineering, 116(4), 904-911 (2019-01-01)
L-Fucose (6-deoxy-L-galactose) is a major constituent of glycans and glycolipids in mammals. Fucosylation of glycans can confer unique functional properties and may be an economical way to manufacture L-fucose. Research can extract L-fucose directly from brown algae, or by enzymatic
Barbara Bolgiano et al.
Pathogens (Basel, Switzerland), 10(8) (2021-08-29)
Towards achieving the goal of eliminating epidemic outbreaks of meningococcal disease in the African meningitis belt, a pentavalent glycoconjugate vaccine (NmCV-5) has been developed to protect against Neisseria meningitidis serogroups A, C, Y, W and X. MenA and X polysaccharides
Krzysztof Brzezinski et al.
Acta crystallographica. Section D, Biological crystallography, 68(Pt 2), 160-168 (2012-01-28)
Rhizobial NodZ α1,6-fucosyltransferase (α1,6-FucT) catalyzes the transfer of the fucose (Fuc) moiety from guanosine 5'-diphosphate-β-L-fucose to the reducing end of the chitin oligosaccharide core during Nod-factor (NF) biosynthesis. NF is a key signalling molecule required for successful symbiosis with a
Feng Gu et al.
Bioresource technology, 149, 375-382 (2013-10-17)
Green liquor (Na2S+Na2CO3, GL) pretreatment is a proven pathway to improve the enzymatic saccharification for the production of bioethanol. In this work, the effects of GL pretreatment on the chemical composition and enzymatic digestibility of rice straw at various total
Marcel Tutor Ale et al.
Marine drugs, 9(10), 2106-2130 (2011-11-11)
Seaweeds--or marine macroalgae--notably brown seaweeds in the class Phaeophyceae, contain fucoidan. Fucoidan designates a group of certain fucose-containing sulfated polysaccharides (FCSPs) that have a backbone built of (1→3)-linked α-L-fucopyranosyl or of alternating (1→3)- and (1→4)-linked α-L-fucopyranosyl residues, but also include
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