Sibiromycin: Isolation and Characterization

A comprehensive review of glycosylated bacterial natural products

“…1304–1306 Both are cytotoxic and sibiromycin binds the minor groove of DNA. 1307 Two C-6- O -2′,4′-di- O -methyl-β-D-xylosyl ( 136 ) quinoline alkaloids were isolated from the cyanobacterium Lyngbya 1308,1309 and the same sugar was also found appended at C-4 of malyngamide J cyclohexanone core (a cytotoxin).…”

Structure of sibiromycin.

“…Further investigation showed that both sibiromycin and anhydrosibiromycin are glycosides of a novel branched-chain aminosugar named sibirosamine. Methanolysis of sibiromycin and or anhydrosibiromycin yielded a mixture of the anomeric methyl sibirosaminides, Under conditions of drastic acidic hydrolysis anhydrosibiromycin lost the aminosugar moiety and gave anhydrosibiromycinone (3) as a bright yellow optically inactive crystalline substance, C16H14N2O3, imax 290, 375, 410 and 435 nm. In Table 1 The most significant evidence which permitted elucidation of the structure of anydrosibiromycinone was obtained from studying the products of alkaline hydrolysis of the dimethyl ether The structure of the acid 9 was determined as 3,5-dimethoxy-4-methylanthranilic acid.…”

Entwicklung Pyrrolobenzodiazepin(PBD)‐haltiger Antikörper‐Wirkstoff‐Konjugate (ADCs) ausgehend von Anthramycin

“…Im Allgemeinen haben PBD-Monomere mit C2-exo-oder C2-endo-Ungesättigtheit (z. B. Anthramycin, [30] Tomaymycin [46] und Sibiromycin [47] ) eine hçhere DNA-Bindungsaffinität als PBD-Monomere mit vollständig gesättig-tem C-Ring (z. B. Neothramycin A, [48] Chicamycin [49] und DC-81 [1a] ).…”