128121-02-8Relevant academic research and scientific papers
Stereoselective synthesis of vinylogous peptides
Grison, Claude,Genève, Stéphane,Halbin, Etienne,Coutrot, Philippe
, p. 4903 - 4923 (2001)
A trans or cis ethenyl group has been inserted between the α-carbon and the carboxyl group of α-aminoacids by Horner stereoselective olefination of α-aminoaldehydes. Numerous pure cis and trans vinylogous α-aminoacids have been obtained thus and coupled w
Structural investigation of "cis" and "trans" vinylogous peptides: cis-vinylog turn in folded cis-vinylogous peptides, an excellent mimic of the natural β-turn
Grison, Claude,Coutrot, Philippe,Geneve, Stephane,Didierjean, Claude,Marraud, Michel
, p. 10753 - 10764 (2005)
Various sequences of modified peptides including those containing a cis- or trans-vinylogous residue have been studied using X-ray diffraction in the solid state and 1H NMR and IR spectroscopy in solution. A cis-vinylogous residue promotes an NH to CO intramolecular H-bond, closing a nine-membered pseudocycle that stabilizes a folded moiety that we proposed to name the cis-vinylogous turn. A trans-vinylogous residue involves an extended conformation. Two consecutive vinylogous residues retain their own structural propensity: "Xaatr"-"Xaacis" or "Xaacis"-"Xaatr" sequence is singly folded, whereas "Xaacis"-"Xaacis" sequence is doubly folded. Oligo vinylogs with all-trans or all-cis or alternating cis-trans motifs could constitute new classes of foldamers.
