81 新抗生物質Glysperin (Bu-2349)の構造

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Glysperin (Bu-2349) is a complex of basic, water-soluble antibiotics produced by a strain of Bacillus cereus. The antibiotic complex comprises three components, A (1a), B (1b) and C (1c). They showed potent antibacterial activity against gram-positive and gram-negative organisms, 1a being the major and most active component. The structures of 1a, 1b and 1c were determined on the basis of chemical degradation studies in conjugation with spectroscopic analyses. 1a (C_<44>H_<75>N_7O_<18>) was shown by acid hydrolysis to contain L-alanine, p-hydroxybenzoic acid, a C_<11>-alkyl tetramine and four sugar moieties. The structure of the C_<11>-amine was determined to be 1,13-diamino-4,9-diazatridecane (8), a new compound, whose structure was confirmed by synthesis. Three of the four sugar moieties were identified as D-ribose, D-galactose and 2,4-diamino-2,4,6-trideoxy-D-galactose. The fourth sugar moiety was a novel exoenohexose and its structure was established as 6-deoxy-D-xylo-hex-5-enose (9) based on the degradation studies performed after catalytic hydrogenation of 1a. The sequence of these structural units in 1a was elucidated by the spectroscopic studies on its partial degradation products. 1b (C_<40>H_<66>N_6O_<18>) was found to possess spermidine in place of 8 in 1a, while 1c (C_<44>H_<77>N_7O_<19>) contained D-glucose instead of 9 in 1a. Glysperins A, B and C are, in some respects, structurally related to the glycocinnamoylspermidine antibiotic LL-BM 123 which was produced by a strain of Nocardia species.
天然有機化合物討論会の論文
1980-09-10

81 新抗生物質Glysperin (Bu-2349)の構造

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