Synthesis of a lividomycin B analogue, 5-O-[3-O-(2-amino-2-deoxy-.ALPHA.-D-glucopyranosyl)-.BETA.-D-ribofuranosyl]-3'-deoxyparomamine.
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概要
- 論文の詳細を見る
5-<I>O</I>-[3-<I>O</I>-(2-Amino-2-deoxy-α-D-glucopyranosyl)-β-D-ribofuranosyl]-3′-deoxyparomamine was prepared by two different routes. The first route involves glycosylation of a protected <I>N</I> : 6-<I>O</I>-carbonyl-3′-deoxyparomamine with a protected 3-<I>O</I>-(2-amino-2-deoxy-α-D-glucopyranosyl)ribofuranosyl bromide and subsequent removal of the protecting groups. In the second route, 1-<I>N</I> : 6-<I>O</I>-carbnyl-3′-deoxyparomamine was glycosylated with a protected ribosyl bromide having 3-<I>O</I>-benzylthiocarbonyl group to give a pseudotrisaccharide and, after de-3-<I>O</I>-benzylthiocarbonylation, the product was further condensed with a protected 1-bromide of 2-amino-2-deoxy-D-glucose. This synthesized lividomycin B analogue showed only very weak antibacterial activity and the role of the 6'″-amino group of lividomycin in the action was suggested.
- 公益社団法人 日本化学会の論文
著者
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UMEZAWA HAMAO
Institute of Microbial Chemistry
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Tsuchiya Tsutomu
Institute of Bioorganic Chemistry
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Umezawa Sumio
Institute of Bioorganic Chemistry
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Umezawa Hamao
Institute of Bioorganic Chemistry
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Watanabe Isamu
Institute of Bioorganic Chemistry
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Takase Tsuneyuki
Department of Applied Chemistry, Faculty of Engineering, Keio University
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