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J Am Chem Soc. 2009 Nov 11;131(44):16018-20. doi: 10.1021/ja907233q.

Stereospecific synthesis of conformationally constrained gamma-amino acids: new foldamer building blocks that support helical secondary structure.

Author information

1
Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53706, USA.

Abstract

A highly stereoselective synthesis of novel cyclically constrained gamma-amino acid residues is presented. The key step involves organocatalytic Michael addition of an aldehyde to 1-nitrocyclohexene. After aldehyde reduction, this approach provides optically active beta-substituted delta-nitro alcohols (96-99% ee), which can be converted to gamma-amino acid residues with a variety of substituents at the alpha position. We have used these new building blocks to prepare alpha/gamma-peptide foldamers that adopt a specific helical conformation in solution and in the solid state.

PMID:
19886693
PMCID:
PMC2843141
DOI:
10.1021/ja907233q
[Indexed for MEDLINE]
Free PMC Article

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