TEMPO/TCC as a Chemo Selective Alternative for the Oxidation of Hyaluronic Acid

Please always quote using this URN: urn:nbn:de:bvb:20-opus-248362
  • 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.show moreshow less

Download full text files

Export metadata

Additional Services

Share in Twitter Search Google Scholar Statistics
Metadaten
Author: Junwen Shan, Thomas Böck, Thorsten KellerORCiD, Leonard Forster, Torsten Blunk, Jürgen GrollORCiD, Jörg TeßmarORCiD
URN:urn:nbn:de:bvb:20-opus-248362
Document Type:Journal article
Faculties:Medizinische Fakultät / Klinik und Poliklinik für Unfall-, Hand-, Plastische und Wiederherstellungschirurgie (Chirurgische Klinik II)
Medizinische Fakultät / Abteilung für Funktionswerkstoffe der Medizin und der Zahnheilkunde
Language:English
Parent Title (English):Molecules
ISSN:1420-3049
Year of Completion:2021
Volume:26
Issue:19
Article Number:5963
Source:Molecules 2021, 26(19), 5963; https://doi.org/10.3390/molecules26195963
DOI:https://doi.org/10.3390/molecules26195963
Dewey Decimal Classification:6 Technik, Medizin, angewandte Wissenschaften / 61 Medizin und Gesundheit / 610 Medizin und Gesundheit
Tag:Schiff base chemistry; hyaluronic acid; hydrogel formation; oxidation
Release Date:2022/01/31
Date of first Publication:2021/10/01
Open-Access-Publikationsfonds / Förderzeitraum 2021
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung