title: Photoinduced Thiol-ene Chemistry Applied to the Synthesis of Self-Assembling Elastin-Inspired Glycopeptides.
abstract: Synthetic (glyco)peptides inspired by proteins able to self-assemble are appealing biomaterials in the field of tissue engineering and regenerative medicine. Herein, for the first time, taking advantage of thiol-ene chemistry coupled to solid-phase peptide synthesis, a self-assembling peptide inspired by elastin protein was bioconjugated to three carbohydrates in order to obtain the corresponding glycopeptides. They were studied at the molecular and supramolecular level. The results show that the carbohydrate influences the molecular conformation of the glycopeptide and its self-aggregation properties as well. As future perspective, the results could enable us to tune the final self-aggregation properties of the glycopeptide by changing the sugar moiety.
authors.affiliation: Department of Science, University of Basilicata, Via Ateneo Lucano, 10, 85100, Potenza, Italy.
authors.forename: Germano
authors.initials: G
authors.lastname: Piccirillo
authors.affiliation: Department of Science, University of Basilicata, Via Ateneo Lucano, 10, 85100, Potenza, Italy.
authors.forename: Antonietta
authors.identifier: http://orcid.org/0000-0002-1285-2273
authors.initials: A
authors.lastname: Pepe
authors.affiliation: Department of Chemical Sciences, University of Naples Federico II, Complesso Universitario Monte S.Angelo, Via Cintia, 4, 80126, Naples, Italy.
authors.forename: Emiliano
authors.identifier: http://orcid.org/0000-0003-4923-3756
authors.initials: E
authors.lastname: Bedini
authors.affiliation: Department of Science, University of Basilicata, Via Ateneo Lucano, 10, 85100, Potenza, Italy.
authors.forename: Brigida
authors.identifier: http://orcid.org/0000-0002-0700-9257
authors.initials: B
authors.lastname: Bochicchio
mesh_terms: D000595:Amino Acid Sequence; D002241:Carbohydrates / Q000737:chemistry; D002942:Circular Dichroism; D004549:Elastin / Q000737:chemistry*; D006020:Glycopeptides / Q000138:chemical synthesis / Q000737:chemistry*; D018625:Microscopy, Atomic Force; D008855:Microscopy, Electron, Scanning; D046529:Microscopy, Electron, Transmission; D012210:Rhamnose / Q000737:chemistry; D060327:Solid-Phase Synthesis Techniques; D017550:Spectroscopy, Fourier Transform Infrared; D013438:Sulfhydryl Compounds / Q000737:chemistry*; D013696:Temperature
chemical_list: D002241:Carbohydrates; D006020:Glycopeptides; D013438:Sulfhydryl Compounds; D004549:Elastin; D012210:Rhamnose
keywords: atomic force microscopy; circular dichroism; elastin; glycopeptides; self-assembly