South African Journal of Chemistry
On-line version ISSN 1996-840X
Print version ISSN 0379-4350
ELIDRISI, Iman et al. Synthesis and NMR elucidation of novel octa-amino acid resorcinarenes derivatives. S.Afr.j.chem. (Online) [online]. 2015, vol.68, pp.27-38. ISSN 1996-840X. http://dx.doi.org/10.17159/0379-4350/2015/v68a5.
The synthesis of nine novel protected amino acid cavitands is reported. All have four pendant M-undecyl chains and 'headgroups' connected by a two-carbon spacer at eight positions on the aromatic rings. The amino acids employed are glycine, alanine, phenylalanine, leucine, proline, tryptophan, serine, glutamine and lysine. The structures of the compounds were elucidated using one and two-dimensional NMR techniques which verified that all octa-substituted cavitands have symmetrical C2vconformation at room temperature. These compounds have potential synthetic ion channel applications.
Keywords : Octa-amino acid resorcinarenes; 1H-NMR; COSY; HSQC; C4v symmetry; C2v symmetry.