Synthesis of a ketomethylene isostere of the fibrillating peptide SNNFGAILSS.
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).
Mittag
Tina
T
The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.
Otzen
Daniel E
DE
Nielsen
Niels Chr
NC
Skrydstrup
Troels
T
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
D000682:Amyloid; D005030:Ethylenes; D007659:Ketones; D009842:Oligopeptides; D010455:Peptides