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J Org Chem. 2009 Oct 16;74(20):7955-7. doi: 10.1021/jo901466b.

Synthesis of a ketomethylene isostere of the fibrillating peptide SNNFGAILSS.

Author information

1
The Center for Insoluble Protein Structures (inSPIN), Department of Chemistry, Aarhus University, Langelandsgade 140, 8000 Aarhus C, Denmark.

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).

PMID:
19739614
DOI:
10.1021/jo901466b
[Indexed for MEDLINE]

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