title: Paleo-soraphens: chemical total syntheses and biological studies.
abstract: The soraphens are natural products that exhibit a molecular structure different from what would have been expected by following its polyketidal assembly line. The most significant differences are the presence of a hemiketal instead of a trisubstituted double bond and a double bond at C9 and C10 where a saturated carbon chain was expected. We were interested in the biological activity of the soraphens with architectures as described by the polyketide synthase since we hypothesized that these modifications reflect the evolutionary optimization of the soraphens. Herein we describe four additional derivatives of the so-called paleo-soraphens and their biological profiling to provide a picture of the hypothetical evolutionary optimization of this family of natural products. The syntheses required a unified and convergent strategy and their biological profiling was performed with the aid of impedance measurements. The results of these biological experiments are consistent with the proposed evolutionary optimization of the soraphens.
authors.affiliation: Institute for Organic Chemistry and Centre for Biomolecular Drug Research (BMWZ), Leibniz Universität Hannover, Schneiderberg 1B, 30167 Hannover, Germany. Markus.Kalesse@oci.uni-hannover.de.
authors.forename: Hai-Hua
authors.initials: HH
authors.lastname: Lu
authors.forename: Bettina
authors.initials: B
authors.lastname: Hinkelmann
authors.forename: Thomas
authors.initials: T
authors.lastname: Tautz
authors.forename: Jun
authors.initials: J
authors.lastname: Li
authors.forename: Florenz
authors.initials: F
authors.lastname: Sasse
authors.forename: Raimo
authors.initials: R
authors.lastname: Franke
authors.forename: Markus
authors.initials: M
authors.lastname: Kalesse
mesh_terms: D000818:Animals; D002460:Cell Line; D016000:Cluster Analysis; D017097:Electric Impedance; D007700:Kinetics; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D051379:Mice; D008968:Molecular Conformation; D013237:Stereoisomerism
chemical_list: D018942:Macrolides; C086151:soraphen A