4 グルコースとオキサロ酢酸とのアルドール縮合によるシアル酸およびその異性体の合成(口頭発表の部)
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概要
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Sialic acid (N-acetylneuraminic acid) is an essential component of ganglioside (sialoglycosphingolipid) which is involved in cellular interactions, differentiation, and growth. Many syntheses of sialic acid using chemical and enzymatic methods were reported. However, the practical synthetic method has not been developed yet. In order to supply enough amount of sialic acid we exploited a convenient chemical synthesis through aldol condensation of D-glucose with oxalacetic acid in relatively short steps. Pyranose (1) was converted to 1,5-lactone to distinguish 5-hydroxyl group from other hydroxyl groups in protection and then introduced an acetylamino group at C5-position with Walden's inversion. Finally, deprotection of all of protecting groups was performed to give N-acetylneuraminic acid. Synthetic N-acetylneuraminic acid was completely identical with natural one in all respects. This synthetic method may supply enough amount of sialic acid from commonly available starting materials. The furanose isomers (2) and (3) as aldol condensation products were also converted to corresponding 1,6-lactones and then transformed into the sialic acid isomers (4) and (5) respectively in the similar way. These furanose isomers with 6-acetylamino group, especially compound (4) with the same stereochemistry at C4 as that of N-acetylneuraminic acid, exhibit remarkable inhibitory activities against neuraminidases of influenza virus A, A2, and B. Therefore, the isomer (4) or (5) is promising as a new anti-influenza drug.
- 天然有機化合物討論会の論文
- 1992-09-10
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