F2252

Sigma-Aldrich

L-(−)-Fucose

≥99%

Synonym(s):
6-Deoxy-L-galactose
Empirical Formula (Hill Notation):
C6H12O5
CAS Number:
Molecular Weight:
164.16
Beilstein/REAXYS Number:
1723321
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

assay

≥99%

form

powder

application(s)

gas chromatography (GC): suitable

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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Application

L-Fucose (6-Deoxy-L-galactose) is used in studies of fucoidan polysaccharide containing glycans. L-Fucose 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 the fucosidase(s), l-fucose isomerase(s) and L-fucose dehydrogenase(s). L-Fucose may be used to study organelles, bacterial microcompartments, involved in the degradation of plant and algal cell wall sugars. L-Fucose may be used as a reference compound in rare sugar identification and analysis.

Packaging

10 mg in glass bottle
5, 25, 100 g in poly bottle

storage_class_code

11 - Combustible Solids

WGK Germany

WGK 3

Flash Point F

Not applicable

Flash Point C

Not applicable

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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...
Cédric Chauvierre et al.
Marine drugs, 17(12) (2019-12-18)
The adhesion molecule P-selectin is present on the cell surface of both activated endothelium and activated platelets. The present study describes the pharmaceutical development, safety evaluation, and preclinical efficacy of a micro-dosed radiotracer. The macromolecular nanoscale assembly consisted of 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...
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...

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