80 Proteus mirabilis lipid Aの全合成
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概要
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Lipid A, a constituent of the lipopolysaccharide (LPS) of Gram-negative bacteria, plays an important role in the various biological activities of LPS. Recent chemical analyses revealed that lipid A contains a central backbone of a 1,6-linked D-glucosamine disaccharide substituted by phosphate groups and by ester- and amide-bound fatty acids. On the basis of these results, we have been developed a generally applicable route for the synthesis of lipid As and the related compounds. 1) Syntheses of lipid As and the related compounds Our methodology includes new development of A, B, C as the general key intermediate for the synthesis of lipid As. Amino and hydroxyl groups of A, B, C can be chemically distinguishable from each other and easily convertible into the required substituents for lipid As. i) Successful conversion of A into lipid X, the synthesis of lipid Y by the chemoselective debenzylation of the glucosamine derivatives via B. ii) Efficient conversion of B into several 4-phosphorylated monosaccharide, nonreducing units of lipid As and KDO α(2→6) linked 4-monophosphate analogues. iii) A formal synthesis of Salmonella mutant lipid A by the common key intermediate. 2) Synthesis of Proteus mirabilis lipid A We have recently developed a practically improved method for synthesis of the common key intermediate D as shown in scheme 1. The disaccharide D, which is a synthetic equivalent to C, is capable of direct conversion into several lipid As. In present abstract, we describe an application of the key intermediate D to a total synthesis of Proteus mirabilis lipid A as indicated in schemes 2 and 3.
- 天然有機化合物討論会の論文
- 1986-09-09
著者
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高橋 敏夫
Shizuoka College Of Pharmacy
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阿知波 一雄
静岡薬大
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近藤 浩史
Shizuoka College Of Pharmacy
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池田 潔
静岡薬大
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高橋 敏夫
静岡薬大
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近藤 浩史
静岡薬大
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池田 かおり
Developmental Research Laboratories Shionogi & Co. Ltd.
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