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Abstract
Hyaluronan, the extracellular matrix glycosaminoglycan, is an important structural component of many tissues playing a critical role in a variety of biological contexts. This makes hyaluronan, which can be biotechnologically produced in large scale, an attractive starting polymer for chemical modifications. This review provides a broad overview of different synthesis strategies used for modulating the biological as well as material properties of this polysaccharide. We discuss current advances and challenges of derivatization reactions targeting the primary and secondary hydroxyl groups or carboxylic acid groups and the N-acetyl groups after deamidation. In addition, we give examples for approaches using hyaluronan as biomedical polymer matrix and consequences of chemical modifications on the interaction of hyaluronan with cells via receptor-mediated signaling. Collectively, hyaluronan derivatives play a significant role in biomedical research and applications indicating the great promise for future innovative therapies.
Highlights
Hyaluronan (HA, formerly named hyaluronic acid) is an ionic, non-branched and multifunctional heteropolysaccharide
This review aims to provide a short overview about known and suitable chemical methods to modify the natural GAG, HA, which is of particular interest in the field of tissue regeneration and regenerative medicine
During the last decade, numerous regioselective syntheses routes could be elaborated, which proceed with high control of regioselectivity regarding the degree and the position of substitution along the HA chain as well as with largely preservation of the HA molecular weight
Summary
Hyaluronan (HA, formerly named hyaluronic acid) is an ionic, non-branched and multifunctional heteropolysaccharide. Together with other low- or medium-sulfated representatives (heparan sulfate, chondroitin sulfate, dermatan sulfate, keratan sulfate) and the high-sulfated heparin, the non-sulfated HA belongs to the family of naturally occurring glycosaminoglycan (GAG) biomacromolecules, the so called mucopolysaccharides. GAG are localized inside and on the surface of all cells. They are involved in various biochemical processes such as cell adhesion, growth and proliferation, cell surface binding, wound healing, or tumor metastasis (Dicker et al, 2014). Compared to sulfated GAG, HA is a structurally uniform natural macromolecule and due to established biotechnological production processes it is readily available in higher quantities (Badri et al, 2018). Despite the progress achieved in the total synthesis of complex oligomeric carbohydrates (DeAngelis et al, 2013; Mende et al, 2016; Fittolani et al, 2021), HA represents an ideal starting material for the chemical conversion into other hardly accessible, mainly high-sulfated GAG or carbohydrate-analogous polymeric molecules mimicking their function, e.g., in the interactions with proteins like mediator molecules (e.g. cytokines)
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