The role of the side chain in the conformational and self-assembly patterns of C2-symmetric Val and Phe pseudopeptidic derivatives
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Altres documents de l'autoria: Gorla, Lingaraju; Martí-Centelles, Vicente; Altava, Belen; Burguete, M. Isabel; Luis, Santiago V.
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Mostra el registre complet de l'elementcomunitat-uji-handle:10234/9
comunitat-uji-handle2:10234/7053
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https://doi.org/10.1039/C8CE02088D |
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Títol
The role of the side chain in the conformational and self-assembly patterns of C2-symmetric Val and Phe pseudopeptidic derivativesAutoria
Data de publicació
2019Editor
Royal Society of ChemistryISSN
1466-8033Cita bibliogràfica
GORLA, Lingaraju, et al. The role of the side chain in the conformational and self-assembly patterns of C 2-symmetric Val and Phe pseudopeptidic derivatives. CrystEngComm, 2019, vol. 21, no 14, p. 2398-2408Tipus de document
info:eu-repo/semantics/articleVersió de l'editorial
https://pubs.rsc.org/en/content/articlehtml/2019/ce/c8ce02088dVersió
info:eu-repo/semantics/publishedVersionParaules clau / Matèries
Resum
The self-assembly patterns of a family of C2-symmetric pseudopeptidic compounds have been studied in the crystalline state, analysing the influence of both the nature of the central spacer and that of the side chain ... [+]
The self-assembly patterns of a family of C2-symmetric pseudopeptidic compounds have been studied in the crystalline state, analysing the influence of both the nature of the central spacer and that of the side chain of the amino acid on the observed features. The nature of the side chain of the component amino acid is the most important structural element defining the conformational and self-assembly patterns. The presence of an aromatic side chain, in the case of Phe derivatives, seems to play a key role in defining folded conformations with the aromatic side chain located over the central spacer. The formation of β-sheet-like stacks in crystals is predominant in Val derivatives but not in Phe-derived compounds. Side chains are strongly involved in intermolecular contacts, with isopropyl groups defining preferentially knob-into-hole interactions and aromatic groups of Phe pseudopeptides defining preferentially edge-to-face arrangements. NMR and CD data suggest that the conformational differences observed in the crystalline structures are also present in solution, in particular in polar solvents. [-]
Publicat a
CrystEngComm, 2019, vol. 21, no 14Proyecto de investigación
Spanish MINECO: CTQ2015-68429-R; Generalitat Valenciana: PROMETEO/2016/071); GV for a Santiago Grisolia: GRISOLIA 2012/015Drets d'accés
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