Vibrational circular dichroism of a 2,5-diketopiperazine (DKP) peptide: Evidence for dimer formation in cyclo LL or LD diphenylalanine in the solid state
| Autor: | Anne Zehnacker, Ariel Pérez-Mellor |
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| Přispěvatelé: | Institut des Sciences Moléculaires d'Orsay (ISMO), Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS), SYSIPHE, Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS)-Université Paris-Sud - Paris 11 (UP11)-Centre National de la Recherche Scientifique (CNRS) |
| Rok vydání: | 2017 |
| Předmět: |
Polymers
Stereochemistry Phenylalanine Dimer Peptide Diketopiperazines 010402 general chemistry 01 natural sciences Catalysis Analytical Chemistry chemistry.chemical_compound Phase (matter) Drug Discovery Diphenylalanine Solid-Phase Synthesis Techniques ComputingMilieux_MISCELLANEOUS Spectroscopy Pharmacology chemistry.chemical_classification 010405 organic chemistry Hydrogen bond Circular Dichroism Organic Chemistry Diastereomer Hydrogen Bonding Stereoisomerism Dipeptides 2 5-Diketopiperazine 3. Good health 0104 chemical sciences [CHIM.THEO]Chemical Sciences/Theoretical and/or physical chemistry chemistry Vibrational circular dichroism Peptides |
| Zdroj: | Chirality Chirality, Wiley, 2017, 29 (2), pp.89-96. ⟨10.1002/chir.22674⟩ |
| ISSN: | 0899-0042 1520-636X |
| DOI: | 10.1002/chir.22674 |
| Popis: | 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…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. |
| Databáze: | OpenAIRE |
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