“…The ligand reacted with the hydroxyl groups present in the polymer forming ether bonds. [ 22 ] Since ethylene sulfide is highly toxic, [ 23 ] it has to be removed quantitatively.…”
Section: Synthesis Of Thiolated Poly‐ and Oligosaccharidesmentioning
Due to thiolation of poly‐ and oligosaccharides numerous favorable properties for tissue engineering and wound healing can be introduced. Poly‐ and oligosaccharides can be thiolated via hydroxyl‐to‐thiol conversions or the covalent attachment of sulfhydryl ligands to hydroxyl, carbonic acid or amino groups on them. Since thiolated poly‐ and oligosaccharides can cross‐link via disulfide bonds, they form stable 3D networks with defined microarchitecture, stiffness, elasticity, and degradability. Furthermore, thiol groups can enhance cell adhesion since cells exhibit cysteine‐rich subdomains on their surface that form disulfide bonds with them. Sulfhydryl groups can also participate in cell signaling pathways favoring various cellular processes like proliferation, migration, spreading, and differentiation that are beneficial for tissue engineering and wound healing. In addition, a controlled release of active ingredients such as growth factors being bound via disulfide bonds to thiolated poly‐ and oligosaccharides can be achieved via thiol/disulfide exchange reactions. Over the last two decades, the number of thiolated poly‐ and oligosaccharides such as thiolated hyaluronic acid and thiolated chitosan used for tissue engineering and wound healing has increased tremendously. Within this review, an overview is provided about the chemistry of thiolated poly‐ and oligosaccharides, their key properties, applications and performance in clinical trials and as marketed products.
“…The ligand reacted with the hydroxyl groups present in the polymer forming ether bonds. [ 22 ] Since ethylene sulfide is highly toxic, [ 23 ] it has to be removed quantitatively.…”
Section: Synthesis Of Thiolated Poly‐ and Oligosaccharidesmentioning
Due to thiolation of poly‐ and oligosaccharides numerous favorable properties for tissue engineering and wound healing can be introduced. Poly‐ and oligosaccharides can be thiolated via hydroxyl‐to‐thiol conversions or the covalent attachment of sulfhydryl ligands to hydroxyl, carbonic acid or amino groups on them. Since thiolated poly‐ and oligosaccharides can cross‐link via disulfide bonds, they form stable 3D networks with defined microarchitecture, stiffness, elasticity, and degradability. Furthermore, thiol groups can enhance cell adhesion since cells exhibit cysteine‐rich subdomains on their surface that form disulfide bonds with them. Sulfhydryl groups can also participate in cell signaling pathways favoring various cellular processes like proliferation, migration, spreading, and differentiation that are beneficial for tissue engineering and wound healing. In addition, a controlled release of active ingredients such as growth factors being bound via disulfide bonds to thiolated poly‐ and oligosaccharides can be achieved via thiol/disulfide exchange reactions. Over the last two decades, the number of thiolated poly‐ and oligosaccharides such as thiolated hyaluronic acid and thiolated chitosan used for tissue engineering and wound healing has increased tremendously. Within this review, an overview is provided about the chemistry of thiolated poly‐ and oligosaccharides, their key properties, applications and performance in clinical trials and as marketed products.
“…Simple ethylene sulfide 6e provided a lower yield of 8e (46%). However, this result has to be put in perspective with the known tendency of 7e to polymerize, as well as its low boiling point (55 °C) . When the reaction was performed with unsymmetrical propylene sulfide, 8f was obtained as a mixture of regioisomers (2.1:1 rr), the major one resulting from the attack of the carboxylate at the most substituted position.…”
We report the oxyalkynylation of thiiranes and thietanes using ethynylbenziodoxolone reagents (EBXs) to readily access functionalized building blocks bearing an alkynyl, a benzoate, and an iodide group. The reaction proceeds with high atom efficiency most likely through an alkynyl−episulfonium intermediate. The transformation is copper-catalyzed and compatible with a large array of thiiranes and thietanes.
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