L-Fucose,
L-岩藻糖
CAS: 2438-80-4
C6H12O5 / 164.16
MFCD00135607
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.
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. 2â -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: 2438-80-4
CAS Name: 6-Deoxy-L-galactose
Additional Names: L-galactomethylose
Molecular Formula: C6H12O5
Molecular Weight: 164.16
Percent 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-Form
Properties: 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 Number | 2438-80-4 |
Product Name | L-(-)-Fucose |
IUPAC Name | (2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal |
Molecular Formula | C6H12O5 |
Molecular Weight | 164.16 g/mol |
InChI | 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 | SHZGCJCMOBCMKK-FPRJBGLDSA-N |
SMILES | CC(C(C(C(C=O)O)O)O)O |
Solubility | Soluble in DMSO |
Synonyms | alpha Fucose, alpha-Fucose, Deoxygalactose, Fucose |
Canonical SMILES | CC(C(C(C(C=O)O)O)O)O |
Isomeric SMILES | C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O)O)O)O |
CAS No: 2438-80-4,6696-41-9 Synonyms: 6-Deoxy-L-galactoseL-(-)-Rhodeose MDL No: MFCD00135607 Chemical Formula: C6H12O5 Molecular Weight: 164.16 | In Stock, 现货高纯,白色结晶粉末. |
COA: |
Name: L-Fucose M.F.: C6H12O5 M.W.: 164.16 CAS: 2438-80-4,6696-41-9
Items | Standards | Results |
Appearance | White crystalline powder | Positive |
Solubility | Readily soluble in water and insoluble in ether | Positive |
NMR and MS | Should comply | Complies |
Identification | IR and TLC | Positive |
M.P. | 130 ℃ –140℃ | 131 ℃ –134 ℃ |
Specific rotation | -74° to -77° | -75.3° |
Loss Weight On Dryness | Max. 1% | Complies |
TLC | One spot | Complies |
Assay (HPLC) | Min. 98% | 99.5% |
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)
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