4279. l-Fucose

Nomenclature

CAS number: 2438-80-4
6-Deoxy-l-galactose; l-galactomethylose.
C6H12O5; mol wt 164.16.
C 43.90%, H 7.37%, O 48.73%.

Description and 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).

Chemical structure

Derivative

α-Form.

Properties

Minute needles from abs alcohol, mp 140°. Shows mutarotation. [α]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.