title: Synthesis and biological evaluation of gramicidin S-inspired cyclic mixed α/β-peptides.
abstract: Via a Mannich reaction involving a dibenzyliminium species and the titanium enolates of Evans' chiral acylated oxazolidinones the β(2)-amino acids (R)- and (S)-Fmoc-β(2)homovaline and (R)-Fmoc-β(2)homoleucine are synthesized. These building blocks were used, in combination with commercially available α- and β(3)-amino acids, for the synthesis of the cyclo-(αβ(3)αβ(2)α)(2) peptide 2 and the cyclo-(αβ(2)αβ(3)α)(2) peptides 3-5. The peptides 2-5 were screened for their ability to inhibit a small panel of Gram-negative and Gram-positive bacterial strains.
authors.affiliation: Bio-Organic Synthesis, Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.
authors.forename: Matthijs
authors.initials: M
authors.lastname: van der Knaap
authors.forename: Fatih
authors.initials: F
authors.lastname: Basalan
authors.forename: Henny C
authors.initials: HC
authors.lastname: van de Mei
authors.forename: Henk J
authors.initials: HJ
authors.lastname: Busscher
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Mark
authors.initials: M
authors.lastname: Overhand
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects; D001424:Bacterial Infections / Q000188:drug therapy; D006096:Gramicidin / Q000737:chemistry*; D006801:Humans; D010456:Peptides, Cyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D010456:Peptides, Cyclic; D006096:Gramicidin