TEMPO/TCC as a Chemo Selective Alternative for the Oxidation of Hyaluronic Acid
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- Hyaluronic acid (HA)-based hydrogels are very commonly applied as cell carriers for different approaches in regenerative medicine. HA itself is a well-studied biomolecule that originates from the physiological extracellular matrix (ECM) of mammalians and, due to its acidic polysaccharide structure, offers many different possibilities for suitable chemical modifications which are necessary to control, for example, network formation. Most of these chemical modifications are performed using the free acid function of the polymer and, additionally,Hyaluronic acid (HA)-based hydrogels are very commonly applied as cell carriers for different approaches in regenerative medicine. HA itself is a well-studied biomolecule that originates from the physiological extracellular matrix (ECM) of mammalians and, due to its acidic polysaccharide structure, offers many different possibilities for suitable chemical modifications which are necessary to control, for example, network formation. Most of these chemical modifications are performed using the free acid function of the polymer and, additionally, lead to an undesirable breakdown of the biopolymer’s backbone. An alternative modification of the vicinal diol of the glucuronic acid is oxidation with sodium periodate to generate dialdehydes via a ring opening mechanism that can subsequently be further modified or crosslinked via Schiff base chemistry. Since this oxidation causes a structural destruction of the polysaccharide backbone, it was our intention to study a novel synthesis protocol frequently applied to selectively oxidize the C6 hydroxyl group of saccharides. On the basis of this TEMPO/TCC oxidation, we studied an alternative hydrogel platform based on oxidized HA crosslinked using adipic acid dihydrazide as the crosslinker.…
Autor(en): | Junwen Shan, Thomas Böck, Thorsten KellerORCiD, Leonard Forster, Torsten Blunk, Jürgen GrollORCiD, Jörg TeßmarORCiD |
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URN: | urn:nbn:de:bvb:20-opus-248362 |
Dokumentart: | Artikel / Aufsatz in einer Zeitschrift |
Institute der Universität: | Medizinische Fakultät / Klinik und Poliklinik für Unfall-, Hand-, Plastische und Wiederherstellungschirurgie (Chirurgische Klinik II) |
Medizinische Fakultät / Abteilung für Funktionswerkstoffe der Medizin und der Zahnheilkunde | |
Sprache der Veröffentlichung: | Englisch |
Titel des übergeordneten Werkes / der Zeitschrift (Englisch): | Molecules |
ISSN: | 1420-3049 |
Erscheinungsjahr: | 2021 |
Band / Jahrgang: | 26 |
Heft / Ausgabe: | 19 |
Aufsatznummer: | 5963 |
Originalveröffentlichung / Quelle: | Molecules 2021, 26(19), 5963; https://doi.org/10.3390/molecules26195963 |
DOI: | https://doi.org/10.3390/molecules26195963 |
Allgemeine fachliche Zuordnung (DDC-Klassifikation): | 6 Technik, Medizin, angewandte Wissenschaften / 61 Medizin und Gesundheit / 610 Medizin und Gesundheit |
Freie Schlagwort(e): | Schiff base chemistry; hyaluronic acid; hydrogel formation; oxidation |
Datum der Freischaltung: | 31.01.2022 |
Datum der Erstveröffentlichung: | 01.10.2021 |
Open-Access-Publikationsfonds / Förderzeitraum 2021 | |
Lizenz (Deutsch): | CC BY: Creative-Commons-Lizenz: Namensnennung |