1146541-31-2Relevant academic research and scientific papers
Synthesis of Ψ[CH(RF)NH]Gly-peptides: The dramatic effect of a single fluorine atom on the diastereocontrol of the key aza-Michael reaction
Bigotti, Serena,Meille, Stefano V.,Volonterio, Alessandro,Zanda, Matteo
, p. 767 - 774 (2008)
We describe in full-detail the synthesis of new ψ[CH(RF)NH]-peptidomimetics, having different fluoroalkyl groups RF, as peptide bond surrogates. A key step in the synthesis is a stereoselective aza-Michael addition of chiral α-amino acid esters to β-fluoroalkyl-α-nitroethenes. The diastereoselection of the process was influenced by the electronegativity, rather than by the steric bulk, of the fluorinated residue RF in the β-position of the nitroalkene acceptors. Replacement of a single F atom of RF by a hydrogen or methyl group brings about a dramatic drop of stereocontrol, whereas Br, Cl and CF3, albeit bulkier than F, provide inferior results in terms of stereocontrol. A mechanistic hypothesis is provided.
The influence of fluoroalkyl-group electronegativity on stereocontrol in the synthesis of ψ[CH(RF)NH]Gly peptides
Bigotti, Serena,Volonterio, Alessandro,Zanda, Matteo
experimental part, p. 958 - 962 (2009/04/11)
New peptidomimetics featuring CH(RF)NH units, having different degree of fluorination, as peptide-bond surrogates have been synthesized. The key step in the synthesis consists of a stereo-selective aza-Michael addition of chiral α-amino acid es
