Isolation of DL-fucosamine from Pseudomonas aeruginosa N10

Biochimica et Biophysica Acta (BBA) - General Subjects
1969.0

Abstract

OD-Fucosamine was isolated from Chromobacterium violaceum (NCTC 7917) in 1958, and subsequently D-fucosamine was found in Bacillus licheniformis, Bacillus subtilis, Bacillus cereus and an unidentified Gram-negative bacterium, while L-fucosamine was detected in type V Pneumococcus capsular polysaccharide and mucopolysaccharide of Citrobacter freundii 05: H30. The present report deals with the isolation of DL-fucosamine from Pseudomonas aeruginosa N10. Bacteria were inoculated in nutrient broth, grown, harvested, hydrolysed with 4 M HCl, and the hydrolysate was purified via Dowex 50-HW-X8, Dowex 50-K and Dowex 50-H column chromatography, then crystallized with acetone. The compound was analysed by elemental analysis (matching C6H14NO4Cl·H2O), optical activity (approx 0), Rondle-Morgan test, deamination, periodate oxidation (consuming 4 moles of periodate and producing 3 moles of formic acid and 1 mole of acetaldehyde per mole), NMR spectroscopy (showing methyl proton signals at 1.33 ppm and 1.25 ppm, C-1 proton signals at 5.45 ppm and 4.4 ppm), paper chromatography (distinguishing from other authentic 2-amino-2,6-dideoxyhexoses) and N-carbobenzoxy derivative identification (matching authentic 2-amino-2,6-dideoxy-D-galactose). Thus, the compound was identified as 2-amino-2,6-dideoxy-DL-galactose (DL-fucosamine) hydrochloride. DL-fucosamine was also isolated from the hydrolysate of a lipopolysaccharide-protein complex of P. aeruginosa N10.

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