A single point chiral inversion that selforganizes a randomcoil peptide. Apolar solvent conformation of Boc-(L/D)-Glu-Ala-Leu-LysNHMe

Article abstract of DOI:10.1016/0040-4020(95)00047-C

The tetrapeptide Boc-L-Glu-Ala-Leu-LysNHMe (1) reveals a random coil conformation, based on its Glu(γ) and Lys(ε) methylene proton aniosotropic shift, GluNH chemical shift, NOEs in the chloroform-DMSO (6:1), and its amide proton temperature coefficients in DMSO, while on similar considerations, the diastereomer Boc-D-Glu-Ala-Leu-LysNHMe (2) is characterized as a highly ordered 3/10 type distorted protohelix with a remarkably stable intramolecular salt bridge under these solvent conditions.