title: Purification and structure elucidation of the by-product of new regulator of antibiotic production and differentiation of Streptomyces.
abstract: Streptomyces globisporus 1912, a producer of the antitumor antibiotic landomycin E, forms the new low-molecular signaling molecule N-methylphenylalanyl-dehydrobutyrine diketopiperazine (BDD) and its complex and unstable by-product which restore, like the A-factor in Streptomyces griseus 773, landomycin E and streptomycin biosynthesis, and sporulation of the defective mutants S. globisporus 1912-B2 and S. griseus 1439, respectively. Here, we report the purification and structure elucidation of two compounds with R(f)0.8 by HPLC, LC/MS and 1HMR analysis. These compounds have m/z 338 and 384, accordingly, and each of them is presented by two stereoisomers containing BDD in their structure. A hypothesis explaining the composition and regulatory properties of these unstable compounds is presented.
authors.affiliation: Zabolotny Institute of Microbiology and Virology, National Academy of Sciences of Ukraine, 154 Acad. Zabolotny St., Kyiv D 03680, Ukraine.
authors.forename: B
authors.initials: B
authors.lastname: Matselyukh
authors.forename: F
authors.initials: F
authors.lastname: Mohammadipanah
authors.forename: H
authors.initials: H
authors.lastname: Laatsch
authors.forename: J
authors.initials: J
authors.lastname: Rohr
authors.forename: O
authors.initials: O
authors.lastname: Efremenkova
authors.forename: V
authors.initials: V
authors.lastname: Khilya
mesh_terms: D000617:Aminoglycosides / Q000096:biosynthesis* / Q000235:genetics; D000903:Antibiotics, Antineoplastic; D001685:Biological Factors / Q000096:biosynthesis / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003470:Culture Media; D013058:Mass Spectrometry; D008970:Molecular Weight; D009154:Mutation; D019906:Nuclear Magnetic Resonance, Biomolecular; D010879:Piperazines / Q000302:isolation & purification* / Q000378:metabolism / Q000494:pharmacology; D015398:Signal Transduction / Q000235:genetics; D013237:Stereoisomerism; D013302:Streptomyces / Q000187:drug effects / Q000235:genetics / Q000378:metabolism*
chemical_list: D000617:Aminoglycosides; D000903:Antibiotics, Antineoplastic; D001685:Biological Factors; D003470:Culture Media; D010879:Piperazines; C113593:landomycin E