title: Synthesis of a ketomethylene isostere of the fibrillating peptide SNNFGAILSS.
abstract: The direct synthesis of a ketomethylene isostere of the fibril-forming decapeptide SNNFGAILSS is presented with the goal of understanding how small structural changes alter the ability of such peptides to recognize each other for beta-sheet formation. The key synthetic step relies on a SmI(2)-mediated coupling of a N-tetrapeptidyl oxazolidinone with a simple acrylate followed by deprotection of the carboxylic acid and a peptide coupling step with the pentapeptide H-AILSS-NH(2).
authors.affiliation: The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
authors.forename: Tina
authors.initials: T
authors.lastname: Mittag
authors.forename: Daniel E
authors.initials: DE
authors.lastname: Otzen
authors.forename: Niels Chr
authors.initials: NC
authors.lastname: Nielsen
authors.forename: Troels
authors.initials: T
authors.lastname: Skrydstrup
mesh_terms: D000595:Amino Acid Sequence; D000682:Amyloid / Q000138:chemical synthesis / Q000737:chemistry; D005030:Ethylenes / Q000737:chemistry*; D007515:Islets of Langerhans / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008969:Molecular Sequence Data; D015394:Molecular Structure; D009842:Oligopeptides; D010455:Peptides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000682:Amyloid; D005030:Ethylenes; D007659:Ketones; D009842:Oligopeptides; D010455:Peptides