Photoinduced Thiol‐ene Chemistry Applied to the Synthesis of Self‐Assembling Elastin‐Inspired Glycopeptides. Issue 11 (27th January 2017)

• Record Type: Journal Article
• Authors: Piccirillo, Germano; Pepe, Antonietta; Bedini, Emiliano; Bochicchio, Brigida
• Is Part Of: Chemistry. Volume 23:Issue 11(2017)
• Page Start: 2648
• Page End: 2659
• Publication Date: 2017-01-27
• Subjects: atomic force microscopy -- circular dichroism -- elastin -- glycopeptides -- self-assembly; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201604831
• Languages: English
• ISSNs: 0947-6539

Abstract

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. Abstract : Sweet in the right light : Glycopeptide synthesis still presents important challenges. The first example of the bioconjugation of a self‐assembling elastin‐inspired peptide and three carbohydrates has been realized exploiting photoinduced thiol‐ene chemistry coupled to solid‐phase peptide synthesis. The self‐assembly of glycopeptide‐triggered nanoaggregate formation is shown by AFM and TEM microscopies.