title: Total synthesis of trans,trans-Sanguinamide B and conformational isomers.
abstract: The first total synthesis of Sanguinamide B is reported, prepared via an efficient synthetic strategy. The natural product, trans,trans-Sanguinamide B (1), was generated in a thermodynamic ratio with trans,cis-Sanguinamide B (2) and cis,cis-Sanguinamide B (3). Complete conversion of the cis,cis-Sanguinamide B conformer (3) to the natural product (1) and the trans,cis- conformer (2) was achieved by heating to 170 °C. Biological evaluation indicated that the Sanguinamide B conformers disrupted the activity of a virulence determinant in P. aeruginosa.
authors.affiliation: Department of Chemistry and Biochemistry, San Diego State University, 5500 Campanile Drive, San Diego, California 92182-1030, USA.
authors.forename: Erinprit K
authors.initials: EK
authors.lastname: Singh
authors.forename: Deborah M
authors.initials: DM
authors.lastname: Ramsey
authors.forename: Shelli R
authors.initials: SR
authors.lastname: McAlpine
mesh_terms: D007536:Isomerism; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000494:pharmacology; D011550:Pseudomonas aeruginosa / Q000187:drug effects / Q000472:pathogenicity; D013844:Thiazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D014774:Virulence
chemical_list: D010080:Oxazoles; D010456:Peptides, Cyclic; D013844:Thiazoles; C572270:sanguinamide B