title: A practical synthesis of gramicidin s and sugar amino Acid containing analogues.
abstract: A practical gram-scale and high-yielding synthesis of the antimicrobial peptide gramicidin S is presented. An Fmoc-based solid-phase peptide synthesis protocol is employed for the generation of the linear decapeptide precursor, which is cyclized in solution to afford the target compound. The versatility of our method is demonstrated by the construction of eight gramicidin S analogues (15a-h) having nonproteinogenic sugar amino acid residues (4-7) incorporated in the turn regions.
authors.affiliation: Leiden Institute of Chemistry, Gorlaeus Laboratories, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Gijsbert M
authors.initials: GM
authors.lastname: Grotenbreg
authors.forename: Martijn
authors.initials: M
authors.lastname: Kronemeijer
authors.forename: Mattie S M
authors.initials: MS
authors.lastname: Timmer
authors.forename: Farid
authors.initials: F
authors.lastname: El Oualid
authors.forename: Renate M
authors.initials: RM
authors.lastname: van Well
authors.forename: Martijn
authors.initials: M
authors.lastname: Verdoes
authors.forename: Emile
authors.initials: E
authors.lastname: Spalburg
authors.forename: Peter A V
authors.initials: PA
authors.lastname: van Hooft
authors.forename: Albert J
authors.initials: AJ
authors.lastname: de Neeling
authors.forename: Daan
authors.initials: D
authors.lastname: Noort
authors.forename: Jacques H
authors.initials: JH
authors.lastname: van Boom
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* / Q000494:pharmacology; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D001409:Bacillus cereus / Q000187:drug effects; D002241:Carbohydrates / Q000138:chemical synthesis* / Q000494:pharmacology; D013293:Enterococcus faecalis / Q000187:drug effects; D004912:Erythrocytes / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D006096:Gramicidin / Q000138:chemical synthesis* / Q000494:pharmacology; D006801:Humans; D008826:Microbial Sensitivity Tests; D013210:Staphylococcus / Q000187:drug effects
chemical_list: D000596:Amino Acids; D000900:Anti-Bacterial Agents; D002241:Carbohydrates; D006096:Gramicidin