{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,3]],"date-time":"2026-04-03T01:19:42Z","timestamp":1775179182497,"version":"3.50.1"},"reference-count":56,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2023,6,6]],"date-time":"2023-06-06T00:00:00Z","timestamp":1686009600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"FCT-Portuguese Foundation for Science and Technology","award":["PTDC\/QUI-QOR\/29015\/2017"],"award-info":[{"award-number":["PTDC\/QUI-QOR\/29015\/2017"]}]},{"name":"FCT-Portuguese Foundation for Science and Technology","award":["CQ\/UM UID\/QUI\/00686\/2013"],"award-info":[{"award-number":["CQ\/UM UID\/QUI\/00686\/2013"]}]},{"name":"FCT-Portuguese Foundation for Science and Technology","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"FCT-Portuguese Foundation for Science and Technology","award":["UID\/CTM\/50025\/2019"],"award-info":[{"award-number":["UID\/CTM\/50025\/2019"]}]},{"name":"FCT-Portuguese Foundation for Science and Technology","award":["CF-UM-UP (UIDB\/04650\/2020)"],"award-info":[{"award-number":["CF-UM-UP (UIDB\/04650\/2020)"]}]},{"name":"FCT-Portuguese Foundation for Science and Technology","award":["022161"],"award-info":[{"award-number":["022161"]}]},{"name":"National NMR Network (PTNMR)","award":["PTDC\/QUI-QOR\/29015\/2017"],"award-info":[{"award-number":["PTDC\/QUI-QOR\/29015\/2017"]}]},{"name":"National NMR Network (PTNMR)","award":["CQ\/UM UID\/QUI\/00686\/2013"],"award-info":[{"award-number":["CQ\/UM UID\/QUI\/00686\/2013"]}]},{"name":"National NMR Network (PTNMR)","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"National NMR Network (PTNMR)","award":["UID\/CTM\/50025\/2019"],"award-info":[{"award-number":["UID\/CTM\/50025\/2019"]}]},{"name":"National NMR Network (PTNMR)","award":["CF-UM-UP (UIDB\/04650\/2020)"],"award-info":[{"award-number":["CF-UM-UP (UIDB\/04650\/2020)"]}]},{"name":"National NMR Network (PTNMR)","award":["022161"],"award-info":[{"award-number":["022161"]}]},{"name":"FEDER","award":["PTDC\/QUI-QOR\/29015\/2017"],"award-info":[{"award-number":["PTDC\/QUI-QOR\/29015\/2017"]}]},{"name":"FEDER","award":["CQ\/UM UID\/QUI\/00686\/2013"],"award-info":[{"award-number":["CQ\/UM UID\/QUI\/00686\/2013"]}]},{"name":"FEDER","award":["UID\/QUI\/0686\/2016"],"award-info":[{"award-number":["UID\/QUI\/0686\/2016"]}]},{"name":"FEDER","award":["UID\/CTM\/50025\/2019"],"award-info":[{"award-number":["UID\/CTM\/50025\/2019"]}]},{"name":"FEDER","award":["CF-UM-UP (UIDB\/04650\/2020)"],"award-info":[{"award-number":["CF-UM-UP (UIDB\/04650\/2020)"]}]},{"name":"FEDER","award":["022161"],"award-info":[{"award-number":["022161"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Gels"],"abstract":"<jats:p>Self-assembled peptide-based hydrogels are archetypical nanostructured materials with a plethora of foreseeable applications in nanomedicine and as biomaterials. N-protected di- and tri-peptides are effective minimalist (molecular) hydrogelators. Independent variation of the capping group, peptide sequence and side chain modifications allows a wide chemical space to be explored and hydrogel properties to be tuned. In this work, we report the synthesis of a focused library of dehydrodipeptides N-protected with 1-naphthoyl and 2-naphthylacetyl groups. The 2-naphthylacetyl group was extensively reported for preparation of peptide-based self-assembled hydrogels, whereas the 1-naphthaloyl group was largely overlooked, owing presumably to the lack of a methylene linker between the naphthalene aromatic ring and the peptide backbone. Interestingly, dehydrodipeptides N-capped with the 1-naphthyl moiety afford stronger gels, at lower concentrations, than the 2-naphthylacetyl-capped dehydrodipeptides. Fluorescence and circular dichroism spectroscopy showed that the self-assembly of the dehydrodipeptides is driven by intermolecular aromatic \u03c0\u2013\u03c0 stacking interactions. Molecular dynamics simulations revealed that the 1-naphthoyl group allows higher order aromatic \u03c0\u2013\u03c0 stacking of the peptide molecules than the 2-naphthylacetyl group, together with hydrogen bonding of the peptide scaffold. The nanostructure of the gel networks was studied by TEM and STEM microscopy and was found to correlate well with the elasticity of the gels. This study contributes to understanding the interplay between peptide and capping group structure on the formation of self-assembled low-molecular-weight peptide hydrogels. Moreover, the results presented here add the 1-naphthoyl group to the palette of capping groups available for the preparation of efficacious low-molecular-weight peptide-based hydrogels.<\/jats:p>","DOI":"10.3390\/gels9060464","type":"journal-article","created":{"date-parts":[[2023,6,7]],"date-time":"2023-06-07T02:02:15Z","timestamp":1686103335000},"page":"464","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":5,"title":["Unveiling the Role of Capping Groups in Naphthalene N-Capped Dehydrodipeptide Hydrogels"],"prefix":"10.3390","volume":"9","author":[{"ORCID":"https:\/\/orcid.org\/0000-0002-8132-9080","authenticated-orcid":false,"given":"Helena","family":"Vila\u00e7a","sequence":"first","affiliation":[{"name":"Centre of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"},{"name":"Department of Chemistry and Biotechnology, Technological Centre for the Textile and Clothing Industries of Portugal, 4760-034 Vila Nova de Famalic\u00e3o, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4816-6371","authenticated-orcid":false,"given":"Andr\u00e9","family":"Carvalho","sequence":"additional","affiliation":[{"name":"Centre of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1040-459X","authenticated-orcid":false,"given":"Tarsila","family":"Castro","sequence":"additional","affiliation":[{"name":"Centre of Biological Engineering, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-5829-6081","authenticated-orcid":false,"given":"Elisabete M. S.","family":"Castanheira","sequence":"additional","affiliation":[{"name":"Physics Centre of Minho and Porto Universities (CF-UM-UP), University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9936-8088","authenticated-orcid":false,"given":"Loic","family":"Hilliou","sequence":"additional","affiliation":[{"name":"Institute for Polymers and Composites, Department of Polymer Engineering, University of Minho, Campus de Azur\u00e9m, 4800-058 Guimar\u00e3es, Portugal"}]},{"given":"Ian","family":"Hamley","sequence":"additional","affiliation":[{"name":"Department of Chemistry, University of Reading, Whiteknights, P.O. Box 224, Reading RG6 6AD, UK"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1929-0477","authenticated-orcid":false,"given":"Manuel","family":"Melle-Franco","sequence":"additional","affiliation":[{"name":"CICECO-Aveiro Institute of Materials, Department of Chemistry, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3279-6731","authenticated-orcid":false,"given":"Paula M. T.","family":"Ferreira","sequence":"additional","affiliation":[{"name":"Centre of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9323-3978","authenticated-orcid":false,"given":"Jos\u00e9 A.","family":"Martins","sequence":"additional","affiliation":[{"name":"Centre of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,6,6]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1038\/s41565-019-0461-7","article-title":"Opportunities and challenges for nanotechnology in the agritech revolution","volume":"14","author":"Lowry","year":"2019","journal-title":"Nat. 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