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Jeng-Liang Han,Bikash Pal,Kuo-Ching Chu,Chien-Tai Ren,Chung-Yi Wu 한국당과학회 2012 한국당과학회 학술대회 Vol.2012 No.1
Polysialic acids, linearly fused N-acetylneuraminic acid (Neu5Ac), play a central role in numerous biological recognition processes such as lymphocyte homing, tumor metathesis, meningitis, urinary tract infections and pathogenic bacteria infections. Three types of polysialic acids, which are different by the internal linkages, have been isolated and identified from the microorganisms. The α (2→8) polysialic acid is a component of neuroinvasive E. coli K1and N. meningitida serogroup B, while the α (2→9) polysialic acid is a component of N. meningitida serogroup C. The alternating α (2→8)/α (2→9) polysialic acid is isolated from E. coli K92 and Bos-12 strains and not found in mammalian systems, making it a potentially carbohydrate vaccine for medicinal treatment. The glycoconjugates of isolated α (2→9) polysialic acid and a carrier protein (ex: diphtheria or tentanus toxoid) are the current vaccines against Meningococcal group C diseases; however, these vaccines are often heterogeneous or contaminated with other antigenic components due to the difficulty in purifying polysialic acids from natural sources. Recently, our lab has successfully and efficiently synthesized α (2→9) polysialic acids up to dodecamers with high yield using 5 -N,4-O-carbonyl protected phosphate-based donors via the convergent block synthesis strategy.