L-Fucose, CAS:2438-80-4

L-FucoseL-(?)-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.Beta-D-Fucose, also known as b-D-fuc or beta-delta-fuc, belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Beta-D-Fucose is soluble (in water) and a very weakly acidic compound (based on its pKa). Within the cell, Beta-D-fucose is primarily located in the cytoplasm. Beta-D-Fucose can be converted into quercetin 3-O-beta-D-fucopyranoside.Beta-D-fucose is a D-fucopyranose with a beta-configuration at the anomeric position. It is an enantiomer of a beta-L-fucose.Fucose (Fuc, 6-deoxy L-galactose) has a methyl group at C6 in place of a hydroxyl group and this gives the molecule a greater degree of hydrophobicity than galactose (Collins, 2006). L-fucose is found in fucoidan, a polysaccharide that occurs in the brown seaweeds (Phaeophyceae) (Percival, 1967). Fucose is also a key component in many mammalian N- and O-linked glycans, glycolipids, blood group substances and Lewis antigens (Becker, 2003). In human milk, neutral (fucosylated) oligosaccharides (HMO) contain fucose at the terminal position (e.g. 2’ -fucosyllactose and lactodifucopentaose). They represent 35% to 50% of the total HMO content and many in vitro studies suggest that HMOs directly modulate immune responses, acting either locally on cells of the mucosa-associated lymphoid tissues or systemically to inhibit the expression of inflammatory genes, mainly cytokines (Plaza-Diaz, 2018).Title:?L-Fucose
CAS Registry Number:?2438-80-4CAS Name:?6-Deoxy-L-galactoseAdditional Names:?L-galactomethyloseMolecular Formula:?C6H12O5Molecular Weight:?164.16Percent Composition:?C 43.90%, H 7.37%, O 48.73%Literature References:?Occurs in seaweed:?Ascophyllum nodosum?(L.) Ledol.?(Fucus nodosus?L.),?Fucus vesiculosus?L.,?F. serratus?L.,?F. virsoides?(Don) J. Ag.,?Fucaceae,?and in gum tragacanth. Isoln from seaweed: Clark,?J. Biol. Chem.?54,?65 (1922); Hockett?et al.,?J. Am. Chem. Soc.?61,?1658 (1939). Manuf from fucoidan: Schweiger,?US?3240775?(1966 to Kelco). Synthesis from?D-galactose: Dejterjuszynski, Flowers,?Carbohydr. Res.?28,?144 (1973); from?D-glucose: T. Chiba, S. Tejima,?Chem. Pharm. Bull.?27,?2838 (1979); from?D-mannose: J. Defaye?et al.,?Carbohydr. Res.?94,?131 (1981). Review of chemistry and biochemistry: H. M. Flowers,?Adv. Carbohydr. Chem. Biochem.?39,?279-345 (1981).?Derivative Type:?a-FormProperties:?Minute needles from abs alcohol, mp 140?. Shows mutarotation. [a]D20?-124.1? (10 min)???-108.0? (20 min)???-91.5? (36 min)???-78.6? (70 min)???-75.6? (final value, 24 hrs, c = 9). Soluble in water and alcohol.Melting point:?mp 140?Optical Rotation:?[a]D20?-124.1? (10 min)???-108.0? (20 min)???-91.5? (36 min)???-78.6? (70 min)???-75.6? (final value, 24 hrs, c = 9)CAS Number2438-80-4Product NameL-(-)-FucoseIUPAC Name(2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanalMolecular FormulaC6H12O5Molecular Weight164.16 g/molInChIInChI=1S/C6H12O5/c1-3(8)5(10)6(11)4(9)2-7/h2-6,8-11H,1H3/t3-,4+,5+,6-/m0/s1InChI KeySHZGCJCMOBCMKK-FPRJBGLDSA-NSMILESCC(C(C(C(C=O)O)O)O)OSolubilitySoluble in DMSOSynonymsalpha Fucose, alpha-Fucose, Deoxygalactose, FucoseCanonical SMILESCC(C(C(C(C=O)O)O)O)OIsomeric SMILESC[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O)O)O)OCAS No: 2438-80-4,6696-41-9 Synonyms: 6-Deoxy-L-galactoseL-(-)-Rhodeose MDL No: MFCD00135607 Chemical Formula: C6H12O5 Molecular Weight: 164.16In Stock,????,??????.COA:Name:?L-Fucose? ?M.F.: C6H12O5? ??M.W.: 164.16? ??CAS:?2438-80-4,6696-41-9ItemsStandardsResultsAppearanceWhite crystalline powderPositiveSolubilityReadily soluble in water andinsoluble in etherPositiveNMR and MSShould complyCompliesIdentificationIR and TLCPositiveM.P.130????140?131????134??Specific rotation-74???to??-77?-75.4?Loss Weight On DrynessMax. 1%CompliesTLCOne spotCompliesAssay (HPLC)Min. 95%97.6%References:1. Wong C-H, Alajarin R, Morfs-Varas F, Blanco O, Garcia-Junceda E, J. Org. Chem. 1995, 60, p7360-7363
2. Cappi MW, Moree WJ, Qiao L, Marron TG, Weitz G, Bioorg. Med. Chem. 1997, Vol5, No2, p283-296(14)