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  • 6696-41-9 , L-Fucose, L-岩藻糖, CAS:6696-41-9
  • 6696-41-9 , L-Fucose, L-岩藻糖, CAS:6696-41-9
6696-41-9 , L-Fucose, L-岩藻糖, CAS:6696-41-96696-41-9 , L-Fucose, L-岩藻糖, CAS:6696-41-9

6696-41-9 , L-Fucose, L-岩藻糖, CAS:6696-41-9

6696-41-9 , L-Fucose,
L-岩藻糖
CAS: 6696-41-9
C6H12O5 / 164.16
MFCD00135607

L-岩藻糖 , L-Fucose

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. 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: 6696-41-9

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 Number6696-41-9
Product NameL-(-)-Fucose
IUPAC Name(2S,3R,4R,5S)-2,3,4,5-tetrahydroxyhexanal
Molecular FormulaC6H12O5
Molecular Weight164.16 g/mol
InChIInChI=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 KeySHZGCJCMOBCMKK-FPRJBGLDSA-N
SMILESCC(C(C(C(C=O)O)O)O)O
SolubilitySoluble in DMSO
Synonymsalpha Fucose, alpha-Fucose, Deoxygalactose, Fucose
Canonical SMILESCC(C(C(C(C=O)O)O)O)O
Isomeric SMILESC[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

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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°

-75.4°

Loss Weight On Dryness

Max. 1%

Complies

TLC

One spot

Complies

Assay (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)

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