155224-48-9Relevant academic research and scientific papers
γ- and β-Peptide Foldamers from Common Multifaceted Building Blocks: Synthesis and Structural Characterization
Ganesh Kumar, Mothukuri,Gopi, Hosahudya N.
, p. 4738 - 4741 (2015)
Structural characterization of 3,4-disubstituted γ-peptide and 2,3-disubstituted β-peptide foldamers derived from common multifaceted β-nitromethyl γ-amino acids and the chemical transformation of the β-nitromethyl group in γ-peptides into various functio
Synthesis and stereochemical analysis of β-nitromethane substituted γ-amino acids and peptides
Ganesh Kumar, Mothukuri,Mali, Sachitanand M.,Gopi, Hosahudya N.
, p. 803 - 813 (2013/02/25)
The high diastereoselectivity in the Michael addition of nitromethane to α,β-unsaturated γ-amino esters, crystal conformations of β-nitromethane substituted γ-amino acids and peptides are studied. Results suggest that the N-Boc protected amide NH, conformations of α,β-unsaturated γ-amino esters and alkyl side chains play a crucial role in dictating the high diastereoselectivity of nitromethane addition to E-vinylogous amino esters. Investigation of the crystal conformations of both α,β-unsaturated γ-amino esters and the Michael addition products suggests that an H-Cγ-CβC α eclipsed conformer of the unsaturated amino ester leads to the major (anti) product compared to that of an N-Cγ-C βCα eclipsed conformer. The major diastereomers were separated and subjected to the peptide synthesis. The single crystal analysis of the dipeptide containing β-nitromethane substituted γ-amino acids reveals a helical type of folded conformation with an isolated H-bond involving a nine-atom pseudocycle. The Royal Society of Chemistry 2013.
