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Unprotected dipeptides are attractive building blocks for environmentally friendly hydrogel biomaterials by virtue of their low-cost and ease of preparation. This work investigates the self-assembling behaviour of the distinct stereoisomers of Ile-Phe and Phe-Ile in phosphate buffered saline (PBS) to form hydrogels, using transmission electron microscopy (TEM), attenuated total reflectance infrared spectroscopy (ATR-IR), circular dichroism (CD), and oscillatory rheometry. Each peptide purity and identity was also confirmed by 1 H- and 13 C-NMR spectroscopy and HPLC-MS. Finally, single-crystal XRD data allowed the key interactions responsible for the supramolecular packing into amphipathic layers or water-channels to be revealed. The presence of the latter in the crystal structure is a distinctive feature of the only gelator of this work that self-organizes into stable hydrogels, with fast kinetics and the highest elastic modulus amongst its structural isomers and stereoisomers. © 2021 The Authors. ChemBioChem published by Wiley-VCH GmbH.


Ottavia Bellotto, Slavko Kralj, Michele Melchionna, Paolo Pengo, Matic Kisovec, Marjetka Podobnik, Rita De Zorzi, Silvia Marchesan. Self-Assembly of Unprotected Dipeptides into Hydrogels: Water-Channels Make the Difference. Chembiochem : a European journal of chemical biology. 2022 Jan 19;23(2):e202100518

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PMID: 34784433

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