A Fiberlike Peptide Material Stabilized by Single Intermolecular Hydrogen Bonds

Abstract

One is enough: The dipeptide Boc-L-Phe-D-Oxd-OBn (Boc=tert-butoxycarbonyl, Phe=phenylalanine, Oxd=4-methyl-5-carboxy oxazolidin-2-one, Bn=benzyl; see picture; gray C, white H, red O, blue N) spontaneously forms uniform fibers consisting of parallel infinite linear chains arising from single intermolecular NH⋅⋅⋅OC hydrogen bonds. This is the absolute borderline case of a parallel β-sheet structure.