Ontology highlight
ABSTRACT:
SUBMITTER: Guo L
PROVIDER: S-EPMC2843141 | biostudies-literature | 2009 Nov
REPOSITORIES: biostudies-literature
Guo Li L Chi Yonggui Y Almeida Aaron M AM Guzei Ilia A IA Parker Brian K BK Gellman Samuel H SH
Journal of the American Chemical Society 20091101 44
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 foldame ...[more]