Por favor, use este identificador para citar o enlazar a este item:
http://hdl.handle.net/10261/233138
COMPARTIR / EXPORTAR:
SHARE CORE BASE | |
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL | DATACITE | |
Título: | Heterochirality restricts the self-assembly of phenylalanine dipeptides capped with highly aromatic groups |
Autor: | Gil, Ana M. CSIC; Casanovas, Jordi; Mayans, Enric; Jiménez, Ana I. CSIC ORCID; Puiggalí, Jordi; Alemán, Carlos | Fecha de publicación: | 2020 | Editor: | ACS Publications | Citación: | Journal of Physical Chemistry B 124(28): 5913-5918 (2020) | Resumen: | The influence of stereochemistry on the self-assembly of phenylalanine (Phe) dipeptides bearing aromatic fluorenyl groups at both the N- and C-termini (Fmoc, OFm) has been investigated. For this purpose, Fmoc–d-Phe–l-Phe–OFm and Fmoc–l-Phe–l-Phe–OFm have been examined considering a wide variety of solvents, which differ in dielectric constant and volatility. Results reveal that replacement of l-Phe by d-Phe has a major impact on the self-assembly propensities, restricting drastically the structural diversity and polymorphism shown by the homochiral dipeptide. Thus, the analogous heterochiral dipeptide shows a great propensity to form micro/nanofibers, independently of the environmental conditions. Theoretical calculations revealed that the stability of antiparallel disposition is much higher (a factor of ca. 15) for Fmoc–d-Phe–l-Phe–OFm than that for Fmoc–l-Phe–l-Phe–OFm, which has been attributed to the hydrophobic core formed in the former. Overall, results suggest that control of the backbone chirality is a potent and versatile strategy to drive and finely tune the self-assembly propensities of highly aromatic peptides. | Versión del editor: | https://doi.org/10.1021/acs.jpcb.0c04513 | URI: | http://hdl.handle.net/10261/233138 | DOI: | 10.1021/acs.jpcb.0c04513 | E-ISSN: | 1520-5207 |
Aparece en las colecciones: | (ISQCH) Artículos |
Ficheros en este ítem:
Fichero | Descripción | Tamaño | Formato | |
---|---|---|---|---|
accesoRestringido.pdf | 59,24 kB | Adobe PDF | Visualizar/Abrir |
CORE Recommender
SCOPUSTM
Citations
11
checked on 09-abr-2024
WEB OF SCIENCETM
Citations
11
checked on 29-feb-2024
Page view(s)
65
checked on 24-abr-2024
Download(s)
12
checked on 24-abr-2024
Google ScholarTM
Check
Altmetric
Altmetric
NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.