1314654-10-8Relevant academic research and scientific papers
GAMMA AMINO ACID BUILDING BLOCKS
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, (2011/05/05)
The invention provides compounds and methods, for example, to carry out organocatalytic Michael additions of aldehydes to cyclically constrained nitroethylene compounds catalyzed by a pro line derivative to provide cyclically constrained α-substituted-γ-n
Stereospecific synthesis of conformationally constrained γ-amino acids: New foldamer building blocks that support helical secondary structure
Guo, Li,Chi, Yonggui,Almeida, Aaron M.,Guzei, Ilia A.,Parker, Brian K.,Gellman, Samuel H.
supporting information; experimental part, p. 16017 - 16020 (2010/02/15)
(Figure Presented) A highly stereoselective synthesis of novel cyclically constrained γ-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 β-substituted δ-nitro alcohols (96-99% ee), which can be converted to γ-amino acid residues with a variety of substituents at the α position. We have used these new building blocks to prepare α/γ-peptide foldamers that adopt a specific helical conformation in solution and in the solid state. Copyright
