4277. Fucosamine
Nomenclature
CAS number: 24724-90-1
2-Amino-2,6-dideoxygalactose. C6H13NO4; mol wt 163.17.
C 44.17%, H 8.03%, N 8.58%, O 39.22%.
Description and references
Isoln of d-form from lipopolysaccharide of Chromobacterium violaceum: Crumpton, Davies, Biochem. J. 70, 729 (1958); from Bacillus licheniformis: Sharon et al., ibid. 93, 210 (1964). Isoln of l-form from type V Pneumococcus capsular polysaccharide: Barker et al., Nature 189, 303 (1961). Synthesis of l-form: Kuhn et al., Ann. 628, 186 (1959); J. Lehmann et al., Ber. 112, 1470 (1979); of d-form: Zehavi, Sharon, J. Org. Chem. 29, 3654 (1964).
Derivative
d-Form hydrochloride.C6H13NO4.HCl; mol wt 199.63.
C 36.10%, H 7.07%, N 7.02%, O 32.06%, Cl 17.76%.
Properties
Crystals from aq acetone, dec 170-175°. [α]D20 +91° (water). Absorption max: 400 nm.Derivative
N-Acetyl-d-fucosamine.C8H15NO5; mol wt 205.21.
C 46.82%, H 7.37%, N 6.83%, O 38.98%.
Properties
Crystals from ethanol, dec 196-197°. [α]D22 +92° (c = 2 in water).Derivative
l-Form hydrochloride.C6H13NO4.HCl; mol wt 199.63.
C 36.10%, H 7.07%, N 7.02%, O 32.06%, Cl 17.76%.
Properties
Rods from methanol + isopropanol, mp 192-193°. [α]D27 92° (c = 0.89 in water).Derivative
N-Acetyl-l-fucosamine.C8H15NO5; mol wt 205.21.
C 46.82%, H 7.37%, N 6.83%, O 38.98%.