Electrofabrication of large volume di- and tripeptide hydrogels via hydroquinone oxidation

Abstract

The fabrication of protected peptide-based hydrogels on electrode surfaces can be achieved by employing the electrochemical oxidation of hydroquinone to benzoquinone, liberating protons at the electrode-solution interface. The localised reduction...

Mediating Oxidation of Thioethers with Iodine—A Mild and Versatile Pathway to Trigger the Formation of Peptide Hydrogels

“…Exploiting the oxidation of 1,4hydroquinone at the surface of an electrode to generate protons for the gelation of a peptide LMWG, several studies have been published over the last years allowing for various applications of this method. [17] Just recently Adams [18] and co-workers could show that also larger volumes of hydrogel may be realized using this technique. Based on a comparable approach Adams [19] could likewise show that basic solutions of Nap-FF may be gelled upon the addition of dopamine under ambient conditions.…”

Vermittelnde Oxidation von Thioethern mit Iod – Eine vielseitige und milde Methode zur Bildung von Peptidhydrogelen

“…Unter Nutzung dieser elektrochemischen Oxidation für die Gelierung von Peptid-LMWGs sind in den letzten Jahren einige bedeutsame Studien veröffentlicht worden. [17] Erst kürzlich konnten Adams [18] und Mitarbeiter*innen zeigen, dass auch größere Gelvolumina über diese Technik erzeugt werden können. Basierend auf einem vergleichbaren Ansatz der Gruppe um Adams [19] konnten gleichsam basische Lösungen von Nap-FF durch Zugabe von Dopamin unter Umgebungsbedingungen geliert werden.…”

Electrofabrication of a low molecular weight hydrogel at high pH

“…By plotting gel area vs time graphs, we can confirm through linearity of this plot that growth is diffusion controlled and calculate the diffusion coefficient of the rate determining species diffusing from the electrode surface from the slope of this graph. 5 As well as this, when the area becomes invariant with time (zero slope) we can determine the final size of the hydrogel. Photographs of the hydrogels were taken in situ at 30 second intervals for 900 seconds (Figure S6a).…”

“…The size of this zone, and so the size of the hydrogel, is governed by the diffusion distance of the hydrogen or hydroxyl ions. 5 For low molecular weight gelators (LMWG), electrodeposition has been used to form gels at low pH, typically by exploiting the hydroquinone-quinone couple 5,15 or the direct oxidation of water. 16 Gelling at high pH by electrodeposition is yet to be described for a LMWG.…”

“…Previously, we have shown that naphthalene-protected dipeptide gelators such as 2NapVG can form gels via the electrochemical oxidation of hydroquinone which results in a local pH decrease at the electrode surface. 5,13,15 To couple both of these methods, a custom-made H-cell (Figure 4a and Figure S12) was employed, consisting of two glass chambers separated by a Nafion membrane.…”