Journal
CHIRALITY
Volume 29, Issue 2, Pages 89-96Publisher
WILEY
DOI: 10.1002/chir.22674
Keywords
diketopiperazine; DKP; FTIR spectroscopy; hydrogen bond; peptide; VCD; vibrational circular dichroism
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The diastereomer diketopiperazine (DKP) peptides built on phenylalanine, namely, cyclo diphenylalanine LPhe-LPhe and LPhe-DPhe, were studied in the solid phase by vibrational circular dichroism (VCD) coupled to quantum chemical calculations. The unit structure of cyclo LPhe-LPhe in KBr pellets is a dimer bridged by two strong NH center dot center dot center dot O hydrogen bonds. The intense bisignate signature in the CO stretch region is interpreted in terms of two contributions arising from the free COs of the dimer and the antisymmetrical combination of the bound COs. In contrast, cyclo LPhe-DPhe shows no VCD signal in relation to its symmetric nature.
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