The alpha-helix, a major structural protein motif, plays a fundamental role in mediating protein-protein and protein-nucleic acid interactions. In an alpha-helix, a hydrogen bond between the C=O of the ith amino acid residue and the NH of the (i+4)th amino acid residue stabilizes and nucleates the helical structure.  Our strategy for the preparation of artificial alpha-helices involves replacement of the N-terminal main-chain i and i+4 hydrogen bond with a covalent linkage through a ring-closing metathesis reaction.  This method affords preorganized alpha-turns to overcome the nucleation barrier and initiate alpha-helix formation.  This poster will describe the synthetic strategies, structural characterization, and biological applications of hydrogen bond surrogate (HBS) alpha-helices.

Protein and nucleic acid recognition by hydrogen bond surrogate alpha-helices

241st National Meeting (2011)

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