175398-30-8Relevant academic research and scientific papers
The fluoroalkene motif as a surrogate of the amide bond: Syntheses of AA-Ψ[(Z) and (E)-CFCH]-Pro pseudodipeptides and an Enalapril analogue
Villiers, Emilie,Couve-Bonnaire, Samuel,Cahard, Dominique,Pannecoucke, Xavier
, p. 7054 - 7062 (2015)
This work describes the optimization process for the synthesis of pseudodipeptides featuring a proline bound to another amino acid through a fluoroalkene moiety that act as an amide bond surrogate. The synthetic methodology is extended to non-peptidic molecules as demonstrated in the design and synthesis of an Enalapril analogue.
Straightforward asymmetric synthesis of Ala-Ψ[CF=CH]-pro, a proline-containing pseudodipeptide bearing a fluoroolefin as a peptide bond mimic
Dutheuil, Guillaume,Pierry, Camille,Villiers, Emilie,Couve-Bonnaire, Samuel,Pannecoucke, Xavier
, p. 1320 - 1325 (2013)
From ethyl-2-oxocyclopentanecarboxylate, we developed an asymmetric synthesis of the fluorinated dipeptide Ala-Ψ[(Z)CFCH]-Pro analogue of the transoid parent dipeptide. The fluorinated pseudodipeptide could be incorporated into various peptides or proteins for conformational, structural studies and biological activity studies and could also play a relevant role as an enzyme inhibitor.
Inhibition of hepatitis C virus NS5A by fluoro-olefin based γ-turn mimetics
Chang, Wonsuk,Mosley, Ralph T.,Bansal, Shalini,Keilman, Meg,Lam, Angela M.,Furman, Phillip A.,Otto, Michael J.,Sofia, Michael J.
supporting information; experimental part, p. 2938 - 2942 (2012/06/15)
The HCV non-structural protein NS5A has been established as a viable target for the development of direct acting antiviral therapy. From computational modeling studies strong intra-molecular hydrogen bonds were found to be a common structural moiety withi
A chemoenzymatic preparation of both enantiomers of ω-hydroxymethyl-substituted lactones
Buisson, Didier,Azerad, Robert
, p. 9 - 12 (2007/10/03)
(R)- and (S)-δ-hydroxymethyl valerolactone and ε-hydroxymethyl caprolactone were prepared as tert-butyldiphenylsilyl derivatives, in good yield and high enantiomeric purities, in a 5 step sequence, starting from the microbial stereospecific reduction of ethyl 2-oxocyclopentane or 2-oxocyclohexane carboxylates respectively.
