Azasulfurylpeptides are amino acid analogs in which the C<sub>α</sub>H and the carbonyl are replaced respectively by a nitrogen atom and a sulfonyl group. We report a solid-phase method for synthesizing azasulfurylpeptides employing <i>N-</i>aminosulfamide tripeptide building blocks. Azasulfurylpeptide conformation has also been studied by X-ray crystallography in the solid state and circular dichroism spectroscopy in solution. Finally, certain azasulfurylpeptides were found to decrease NF-κB activation induced by the Toll-like receptor-2 specific ligand, fibroblast-stimulating lipopeptide in a CD36 dependent manner. The utility of azasulfurylpeptides for exploring peptide chemical biology will thus be demonstrated by the effective solid-phase method for their synthesis, insight gained from their conformational analysis, and their ability to regulate biological activity.

Azasulfurylpeptide solid-phase synthesis, conformational analysis, and application as modulators of toll-like receptor inflammatory response in macrophages

249th National Meeting (2015)

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