80 アデノマイシンの構造

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Structural elucidation of adenomycin(1), C_<25>H_<39>N_7O_<18>S, an antibiotic active against Mycobacteria, was undertaken by degradative (sheme 1) and spectroscopic studies. Spectral data of uv, ir and nmr revealed that 1 belongs to a new member of adenine nucleoside including two or three sugars and sulfate. Presence of a serine moiety in 1 was demonstrated by alkaline hydrolysis which afforded L-serine and deseryladenomycin(2). Identification of sugars in 1 was performed by acid hydrolysis or methanolysis of 2, which gave adenobiosamine(6)(isolated as its nonaacetate(5)), a disaccharide consisting of L-gulosamine and (-)-chiro-inositol, or methyl α and β adenotrioside(7a,7b), methylglycosides of trisaccharide consisting of 6 and D-ribose, respectively. Presence of ribose in 7a and 7b was elucidated by PRFT experiment of ^<13>C-nmr. Binding site of the ribose, sulfate and serine groups to the adenobiosamine moiety was established by the nmr analyses of NaBH_4 reduced products derived from 1 and 2, viz, adenotriitol (10), adenotriitol sulfate(8) and seryl adenotriitol sulfate(11) as well as periodate oxidation of 8.
天然有機化合物討論会の論文
1980-09-10