1032733-38-2Relevant academic research and scientific papers
Synthesis and characterisation of helical β-peptide architectures that contain (S)-β3-HDOPA(crown ether) derivatives
Dutot, Laurence,Gaucher, Anne,Elkassimi, Khadidja,Drapeau, Jeremy,Wakselman, Michel,Mazaleyrat, Jean-Paul,Peggion, Cristina,Formaggio, Fernando,Toniolo, Claudio
supporting information; experimental part, p. 3154 - 3163 (2009/04/11)
A new set of β-amino acids that carry various crown ether receptors on their side chains of the general formula (S)-β3-HDOPA(crown ether) (HDOPA: homo-3,4-dihydroxyphenylalanine; (crown ether): [15]crown-5 ([15-C-5]), [18]crown-6 ([18-C-6]), [21]crown-7 ([21-C-7]), 1,2-Benzo-[24]crown- 8 ([Benzo-24-C-8]) and (R)-Binol-[20]crown-6 ([(R)-Binol-20-C-6])) was prepared. Peptides that are based on these new crowned β-amino acids combined with (1S,2S)-ACHC (2-aminocyclohexanecarboxylic acid), which is known to be a potent 314-helix inducer, to the hexamer level, with two crowned residues at the i and i+3 posi_tions of the main-chain, were synthesized in solution by stepwise coupling using Boc-Na-protection (Boc: tert-butoxycarbonyl) and the EDC/HOAt Cactivation method. Their conformational analysis was performed by using FTIR absorption, NMR and CD spectroscopy techniques. Our results are in full agreement with a 314-helix conformation.
