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Self-assembly of tetraphenylalanine peptides

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10.1002/chem.201501793
 
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Mayans Tayadella, EnricMés informacióMés informació
Ballano Ballano, María Gema
Casanovas Salas, JordiMés informació
Díaz Andrade, Angélica María
Pérez Madrigal, Maria del MarMés informacióMés informacióMés informació
Estrany Coda, FrancescMés informacióMés informacióMés informació
Puiggalí Bellalta, JordiMés informacióMés informacióMés informació
Cativiela Marín, Carlos A.
Alemán Llansó, CarlosMés informacióMés informacióMés informació
Document typeArticle
Defense date2015-11-01
Rights accessRestricted access - publisher's policy
Attribution-NonCommercial-NoDerivs 3.0 Spain
This work is protected by the corresponding intellectual and industrial property rights. Except where otherwise noted, its contents are licensed under a Creative Commons license : Attribution-NonCommercial-NoDerivs 3.0 Spain
Abstract
Three different tetraphenylalanine (FFFF) based peptides that differ at the N- and C-termini have been synthesized by using standard procedures to study their ability to form different nanoassemblies under a variety of conditions. The FFFF peptide assembles into nanotubes that show more structural imperfections at the surface than those formed by the diphenylalanine (FF) peptide under the same conditions. Periodic DFT calculations (M06L functional) were used to propose a model that consists of three FFFF molecules defining a ring through head-to-tail NH3 +¿-OOC interactions, which in turn stack to produce deformed channels with internal diameters between 12 and 16 Å. Depending on the experimental conditions used for the peptide incubation, N-fluorenylmethoxycarbonyl (Fmoc) protected FFFF self-assembles into a variety of polymorphs: ultra-thin nanoplates, fibrils, and star-like submicrometric aggregates. DFT calculations indicate that Fmoc-FFFF prefers a parallel rather than an antiparallel ß-sheet assembly. Finally, coexisting multiple assemblies (up to three) were observed for Fmoc-FFFF-OBzl (OBzl = benzyl ester), which incorporates aromatic protecting groups at the two peptide terminals. This unusual and noticeable feature is attributed to the fact that the assemblies obtained by combining the Fmoc and OBzl groups contained in the peptide are isoenergetic. Variety show! Three different tetraphenylalanine-based peptides that differ at the N- and C-termini have been synthesized by using standard procedures to study their ability to form different nanoassemblies (e.g., nanotubes, see figure) under a variety of conditions.
CitationMayans, E., Ballano, G., Casanovas Salas, Jordi, Diaz, A., Pérez-Madrigal, M.M., Estrany, F., Puiggali, J., Cativiela Marín, Carlos A., Aleman, C. Self-assembly of tetraphenylalanine peptides. "Chemistry - A European Journal", 01 Novembre 2015, vol. 21, p. 16895-16905. 
URIhttp://hdl.handle.net/2117/82844
DOI10.1002/chem.201501793
ISSN1521-3765
Publisher versionhttp://onlinelibrary.wiley.com/doi/10.1002/chem.201501793/abstract
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