90(P-28) リポシドマイシン類の合成研究 : 1,4-ジアゼパノン環部の合成と立体配置の決定(ポスター発表の部)

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Liposidomycins (1), found in the culture filtrate and mycelia of Streptomyces griseosporeus by Isono and co-workers in 1985 as a family of novel lipid-containing nucleoside antibiotics, strongly inhibit bacterial peptidoglycan synthesis. The primary site of action of liposidomycin was determined to be at phospho-N-acetylmuramylpentapeptide transferase (Translocase I), the first step in the lipid cycle of peptidoglycan synthesis in the cell wall of E. coli at 0.03μg/mL, which is extremely specific. The structures of liposidomycins were ascribed based on degradation and spectroscopic studies of 2. However, because of the flexibility of the seven-membered ring and the unusual nature of the ring atoms and substituent, the relative and absolute stereochemistry at three carbons on the diazepanone ring (2, 5 and 6) and one in the junction between diazepanone and nucleoside moieties (5') has not been established. With the limited supply of material for further degradation or crystallographic studies, the synthesis of model compounds and degradation product (2) becomes an important tool for structural assignment. Herein we synthesized three liposidomycin 1,4-diazepane-3-one derivatives (3, 4 and 5) and suggested the assignment of the stereochemistry for liposidomycin 1,4-diazeponone-3-one part to be 2(S), 5(S), 6(S) and 5'(S) or its enantiomer. Through the synthesis of these compounds, the construction of the 1,4-diazepane-3-one ring system by intramolecular reductive amination approach and introduction of penta-substituted functional group at N-1, C2, N-4, C5 and C6 positions based on the synthetic application of trifluoroacetimidates are demonstrated. Also their conformational analyses by NMR and MM calculations will be reported. The synthesis of degradation product (6) is in progress.
天然有機化合物討論会の論文
2002-09-01

90(P-28) リポシドマイシン類の合成研究 : 1,4-ジアゼパノン環部の合成と立体配置の決定(ポスター発表の部)

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