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Key Documents

F2252

Sigma-Aldrich

L-(−)-Fucose

≥98% (GC)

Sinonimo/i:

6-Deoxy-L-galactose

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About This Item

Formula empirica (notazione di Hill):
C6H12O5
Numero CAS:
Peso molecolare:
164.16
Beilstein:
1723321
Numero CE:
Numero MDL:
Codice UNSPSC:
12352201
ID PubChem:
NACRES:
NA.25

Livello qualitativo

Saggio

≥98% (GC)

Forma fisica

powder

tecniche

gas chromatography (GC): suitable

Colore

white

Punto di fusione

150-153 °C (lit.)

Solubilità

H2O: soluble 50 mg/mL, clear to very slightly hazy

Stringa SMILE

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
PNNNRSAQSRJVSB-KCDKBNATSA-N

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Descrizione generale

L-Fucose, a natural monosaccharide found in mammals, is an important component of several N- and O-linked glycans and glycolipids.

Applicazioni

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

Azioni biochim/fisiol

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.

Altre note

To gain a comprehensive understanding of our extensive range of Monosaccharides for your research, we encourage you to visit our Carbohydrates Category page.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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Marcel Tutor Ale et al.
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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
Jay J Listinsky et al.
American journal of translational research, 3(4), 292-322 (2011-09-10)
Breast cancer cells incorporate the simple sugar alpha-L-fucose (fucose) into glycoproteins and glycolipids which, in turn, are expressed as part of the malignant phenotype. We have noted that fucose is not simply a bystander molecule, but, in fact, contributes to
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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
Simon N Robinson et al.
Experimental hematology, 40(6), 445-456 (2012-02-07)
Delayed engraftment remains a major hurdle after cord blood (CB) transplantation. It may be due, at least in part, to low fucosylation of cell surface molecules important for homing to the bone marrow microenvironment. Because fucosylation of specific cell surface
Karineh Petrossian et al.
Acta histochemica, 109(6), 491-500 (2007-08-21)
By using a non-cancer and a cancer cell line originally from the same tissue (colon), coupled with testing lectins for cell binding and for their effects on these cell lines in culture, this study describes a simple multi-parameter approach that

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