Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids
Microstructures from small phenylalanine-based peptides have attracted great attention lately because these compounds are considered to be a new class of tunable materials. In spite of the extensive studies on uncapped diphenylalanine and tetraphenylalanine peptides, studies on the self-assembly of...
| Autores: | , , , , , , |
|---|---|
| Tipo de recurso: | artículo |
| Fecha de publicación: | 2017 |
| País: | España |
| Institución: | Universitat Politècnica de Catalunya (UPC) |
| Repositorio: | UPCommons. Portal del coneixement obert de la UPC |
| Idioma: | inglés |
| OAI Identifier: | oai:upcommons.upc.edu:2117/115241 |
| Acceso en línea: | https://hdl.handle.net/2117/115241 https://dx.doi.org/10.1021/acs.langmuir.7b00622 |
| Access Level: | acceso abierto |
| Palabra clave: | Amino acids Peptides Supramolecular chemistry Aminoàcids Química supramolecular Pèptids Àrees temàtiques de la UPC::Enginyeria química |
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Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroidsMayans Tayadella, Enric|||0000-0002-1668-0990Casanovas Salas, Jordi|||0000-0002-4914-9194Gil, Ana M.Jimenez Sanz, Ana IsabelCativiela, CarlosPuiggalí Bellalta, Jordi|||0000-0002-0640-4474Alemán Llansó, Carlos|||0000-0003-4462-6075Amino acidsPeptidesSupramolecular chemistryAminoàcidsQuímica supramolecularPèptidsÀrees temàtiques de la UPC::Enginyeria químicaMicrostructures from small phenylalanine-based peptides have attracted great attention lately because these compounds are considered to be a new class of tunable materials. In spite of the extensive studies on uncapped diphenylalanine and tetraphenylalanine peptides, studies on the self-assembly of uncapped triphenylananine (FFF) are very scarce and nonsystematic. In this work, we demonstrate that FFF assemblies can organize in a wide number of well-defined supramolecular structures, which include laminated helical-ribbons, leaflike dendrimers, doughnut-, needle-, and flower-shapes. These organizations are produced by the attractive or repulsive interactions between already formed assemblies and therefore can be controlled through the choice of solvents used as the incubation medium. Thus, the formation of the desired supramolecular structures is regulated through the protonation/deprotonation of the terminal groups, the polarity of the incubation medium, which affects both peptide···solvent interactions and the cavity solvation energy (i.e., solvent···solvent interactions), and the steric interactions between own assemblies that act as building blocks. Finally, the ß-sheet disposition in the latter structural motifs has been examined using both theoretical calculations and Fourier transform infrared spectroscopy. Results indicate that FFF molecules can adopt both parallel and antiparallel ß-sheets. However, the former one is the most energetically favored because of the formation of p–p stacking interactions between the aromatic rings of hydrogen-bonded strands.20172017-04-0420182018-03-16journal articlehttp://purl.org/coar/resource_type/c_6501AOhttp://purl.org/coar/version/c_b1a7d7d4d402bcceinfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/2117/115241https://dx.doi.org/10.1021/acs.langmuir.7b00622reponame:UPCommons. Portal del coneixement obert de la UPCinstname:Universitat Politècnica de Catalunya (UPC)Inglésengopen accesshttp://purl.org/coar/access_right/c_abf2info:eu-repo/semantics/openAccessoai:upcommons.upc.edu:2117/1152412026-05-27T15:37:01Z |
| dc.title.none.fl_str_mv |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids |
| title |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids |
| spellingShingle |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids Mayans Tayadella, Enric|||0000-0002-1668-0990 Amino acids Peptides Supramolecular chemistry Aminoàcids Química supramolecular Pèptids Àrees temàtiques de la UPC::Enginyeria química |
| title_short |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids |
| title_full |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids |
| title_fullStr |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids |
| title_full_unstemmed |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids |
| title_sort |
Diversity and hierarchy in supramolecular assemblies of triphenylalanine: from laminated helical ribbons to toroids |
| dc.creator.none.fl_str_mv |
Mayans Tayadella, Enric|||0000-0002-1668-0990 Casanovas Salas, Jordi|||0000-0002-4914-9194 Gil, Ana M. Jimenez Sanz, Ana Isabel Cativiela, Carlos Puiggalí Bellalta, Jordi|||0000-0002-0640-4474 Alemán Llansó, Carlos|||0000-0003-4462-6075 |
| author |
Mayans Tayadella, Enric|||0000-0002-1668-0990 |
| author_facet |
Mayans Tayadella, Enric|||0000-0002-1668-0990 Casanovas Salas, Jordi|||0000-0002-4914-9194 Gil, Ana M. Jimenez Sanz, Ana Isabel Cativiela, Carlos Puiggalí Bellalta, Jordi|||0000-0002-0640-4474 Alemán Llansó, Carlos|||0000-0003-4462-6075 |
| author_role |
author |
| author2 |
Casanovas Salas, Jordi|||0000-0002-4914-9194 Gil, Ana M. Jimenez Sanz, Ana Isabel Cativiela, Carlos Puiggalí Bellalta, Jordi|||0000-0002-0640-4474 Alemán Llansó, Carlos|||0000-0003-4462-6075 |
| author2_role |
author author author author author author |
| dc.subject.none.fl_str_mv |
Amino acids Peptides Supramolecular chemistry Aminoàcids Química supramolecular Pèptids Àrees temàtiques de la UPC::Enginyeria química |
| topic |
Amino acids Peptides Supramolecular chemistry Aminoàcids Química supramolecular Pèptids Àrees temàtiques de la UPC::Enginyeria química |
| description |
Microstructures from small phenylalanine-based peptides have attracted great attention lately because these compounds are considered to be a new class of tunable materials. In spite of the extensive studies on uncapped diphenylalanine and tetraphenylalanine peptides, studies on the self-assembly of uncapped triphenylananine (FFF) are very scarce and nonsystematic. In this work, we demonstrate that FFF assemblies can organize in a wide number of well-defined supramolecular structures, which include laminated helical-ribbons, leaflike dendrimers, doughnut-, needle-, and flower-shapes. These organizations are produced by the attractive or repulsive interactions between already formed assemblies and therefore can be controlled through the choice of solvents used as the incubation medium. Thus, the formation of the desired supramolecular structures is regulated through the protonation/deprotonation of the terminal groups, the polarity of the incubation medium, which affects both peptide···solvent interactions and the cavity solvation energy (i.e., solvent···solvent interactions), and the steric interactions between own assemblies that act as building blocks. Finally, the ß-sheet disposition in the latter structural motifs has been examined using both theoretical calculations and Fourier transform infrared spectroscopy. Results indicate that FFF molecules can adopt both parallel and antiparallel ß-sheets. However, the former one is the most energetically favored because of the formation of p–p stacking interactions between the aromatic rings of hydrogen-bonded strands. |
| publishDate |
2017 |
| dc.date.none.fl_str_mv |
2017 2017-04-04 2018 2018-03-16 |
| dc.type.none.fl_str_mv |
journal article http://purl.org/coar/resource_type/c_6501 AO http://purl.org/coar/version/c_b1a7d7d4d402bcce |
| dc.type.openaire.fl_str_mv |
info:eu-repo/semantics/article |
| format |
article |
| dc.identifier.none.fl_str_mv |
https://hdl.handle.net/2117/115241 https://dx.doi.org/10.1021/acs.langmuir.7b00622 |
| url |
https://hdl.handle.net/2117/115241 https://dx.doi.org/10.1021/acs.langmuir.7b00622 |
| dc.language.none.fl_str_mv |
Inglés eng |
| language_invalid_str_mv |
Inglés |
| language |
eng |
| dc.rights.none.fl_str_mv |
open access http://purl.org/coar/access_right/c_abf2 |
| dc.rights.openaire.fl_str_mv |
info:eu-repo/semantics/openAccess |
| rights_invalid_str_mv |
open access http://purl.org/coar/access_right/c_abf2 |
| eu_rights_str_mv |
openAccess |
| dc.format.none.fl_str_mv |
application/pdf |
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reponame:UPCommons. Portal del coneixement obert de la UPC instname:Universitat Politècnica de Catalunya (UPC) |
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Universitat Politècnica de Catalunya (UPC) |
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UPCommons. Portal del coneixement obert de la UPC |
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UPCommons. Portal del coneixement obert de la UPC |
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15,300719 |