title: Purification and structural determination of SCB1, a gamma-butyrolactone that elicits antibiotic production in Streptomyces coelicolor A3(2).
abstract: Early stationary phase culture supernatants of Streptomyces coelicolor A3(2) contained at least four small diffusible signaling molecules that could elicit precocious antibiotic synthesis in the producing strain. The compounds were not detected in exponentially growing cultures. One of these compounds, SCB1, was purified to homogeneity and shown to be a gamma-butyrolactone of structure (2R, 3R,1'R)-2-(1'-hydroxy-6-methylheptyl)-3-hydroxymethylbutanolide . Bioassays of chemically synthesized SCB1, and of its purified stereoisomers, suggest that SCB1 acts in a highly specific manner to elicit the production of both actinorhodin and undecylprodigiosin, the two pigmented antibiotics made by S. coelicolor.
authors.affiliation: Department of Genetics, John Innes Centre, Colney, Norwich NR4 7UH, United Kingdom.
authors.forename: E
authors.initials: E
authors.lastname: Takano
authors.forename: T
authors.initials: T
authors.lastname: Nihira
authors.forename: Y
authors.initials: Y
authors.lastname: Hara
authors.forename: J J
authors.initials: JJ
authors.lastname: Jones
authors.forename: C J
authors.initials: CJ
authors.lastname: Gershater
authors.forename: Y
authors.initials: Y
authors.lastname: Yamada
authors.forename: M
authors.initials: M
authors.lastname: Bibb
mesh_terms: D015107:4-Butyrolactone / Q000138:chemical synthesis / Q000737:chemistry / Q000302:isolation & purification*; D000900:Anti-Bacterial Agents / Q000096:biosynthesis*; D002851:Chromatography, High Pressure Liquid; D013237:Stereoisomerism; D013302:Streptomyces / Q000737:chemistry* / Q000187:drug effects / Q000378:metabolism
chemical_list: D000900:Anti-Bacterial Agents; D015107:4-Butyrolactone