Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility
Polysaccharide derivatives with two types of functionalities were synthesized; reactive groups for click-chemistry approaches and groups that can tune the water solubility of the products. Xylan phenylcarbonates (XPCs) and cellulose phenylcarbonates (CPCs) with degrees of substitution (DS) ranging f...
| Main Authors: | , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Elsevier
2024-06-01
|
| Series: | Carbohydrate Polymer Technologies and Applications |
| Subjects: | |
| Online Access: | http://www.sciencedirect.com/science/article/pii/S2666893924000598 |
| _version_ | 1797249086949163008 |
|---|---|
| author | Martin Gericke Zakaria Atmani Lennart Hendrik Skodda Thomas Heinze |
| author_facet | Martin Gericke Zakaria Atmani Lennart Hendrik Skodda Thomas Heinze |
| author_sort | Martin Gericke |
| collection | DOAJ |
| description | Polysaccharide derivatives with two types of functionalities were synthesized; reactive groups for click-chemistry approaches and groups that can tune the water solubility of the products. Xylan phenylcarbonates (XPCs) and cellulose phenylcarbonates (CPCs) with degrees of substitution (DS) ranging from 0.6 to 3.0 were prepared as starting materials. In a modular synthesis approach, these carbonate derivatives were converted with different amines to obtain functional xylan carbamates (XCs) and cellulose carbamates (CCs) with (i) reactive alkynyl- or furfuryl groups and / or (ii) hydrophilic hydroxyalkyl or tertiary amino groups. Both types of functionalities were introduced separately or simultaneously in a convenient one-pot-approach. Mixed polysaccharide carbamates with low, intermediate, and high DS values (0.6 to 2.5) were successfully prepared and characterized. The water solubility of the carbamates and mixed carbamates was tuned by variation of the type and DS of the two hydrophilic substituents. Surprisingly, some of the products showed lower or upper critical solution temperatures (LCSTs, UCSTs). Thus, the thermoreversible phase transition in aqueous solutions was studied. The products obtained in this work are very promising for the preparation of hydrogels through selective covalent crosslinking as well as for the fabrication of thermoresponsive biomaterials. |
| first_indexed | 2024-04-24T20:24:54Z |
| format | Article |
| id | doaj.art-878ba971eab94c69ad824ddda76962ad |
| institution | Directory Open Access Journal |
| issn | 2666-8939 |
| language | English |
| last_indexed | 2024-04-24T20:24:54Z |
| publishDate | 2024-06-01 |
| publisher | Elsevier |
| record_format | Article |
| series | Carbohydrate Polymer Technologies and Applications |
| spelling | doaj.art-878ba971eab94c69ad824ddda76962ad2024-03-22T05:41:04ZengElsevierCarbohydrate Polymer Technologies and Applications2666-89392024-06-017100479Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubilityMartin Gericke0Zakaria Atmani1Lennart Hendrik Skodda2Thomas Heinze3Corresponding authors.; Friedrich Schiller University of Jena, Institute of Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, GermanyFriedrich Schiller University of Jena, Institute of Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, GermanyFriedrich Schiller University of Jena, Institute of Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, GermanyCorresponding authors.; Friedrich Schiller University of Jena, Institute of Organic Chemistry and Macromolecular Chemistry, Centre of Excellence for Polysaccharide Research, Humboldtstraße 10, D-07743 Jena, GermanyPolysaccharide derivatives with two types of functionalities were synthesized; reactive groups for click-chemistry approaches and groups that can tune the water solubility of the products. Xylan phenylcarbonates (XPCs) and cellulose phenylcarbonates (CPCs) with degrees of substitution (DS) ranging from 0.6 to 3.0 were prepared as starting materials. In a modular synthesis approach, these carbonate derivatives were converted with different amines to obtain functional xylan carbamates (XCs) and cellulose carbamates (CCs) with (i) reactive alkynyl- or furfuryl groups and / or (ii) hydrophilic hydroxyalkyl or tertiary amino groups. Both types of functionalities were introduced separately or simultaneously in a convenient one-pot-approach. Mixed polysaccharide carbamates with low, intermediate, and high DS values (0.6 to 2.5) were successfully prepared and characterized. The water solubility of the carbamates and mixed carbamates was tuned by variation of the type and DS of the two hydrophilic substituents. Surprisingly, some of the products showed lower or upper critical solution temperatures (LCSTs, UCSTs). Thus, the thermoreversible phase transition in aqueous solutions was studied. The products obtained in this work are very promising for the preparation of hydrogels through selective covalent crosslinking as well as for the fabrication of thermoresponsive biomaterials.http://www.sciencedirect.com/science/article/pii/S2666893924000598PolysaccharidesChemical derivatizationPolysaccharide carbamatesStructure characterizationWater solubilityNMR spectroscopy |
| spellingShingle | Martin Gericke Zakaria Atmani Lennart Hendrik Skodda Thomas Heinze Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility Carbohydrate Polymer Technologies and Applications Polysaccharides Chemical derivatization Polysaccharide carbamates Structure characterization Water solubility NMR spectroscopy |
| title | Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility |
| title_full | Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility |
| title_fullStr | Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility |
| title_full_unstemmed | Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility |
| title_short | Synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility |
| title_sort | synthesis and characterization of polysaccharide carbamates and mixed carbamates with tunable water solubility |
| topic | Polysaccharides Chemical derivatization Polysaccharide carbamates Structure characterization Water solubility NMR spectroscopy |
| url | http://www.sciencedirect.com/science/article/pii/S2666893924000598 |
| work_keys_str_mv | AT martingericke synthesisandcharacterizationofpolysaccharidecarbamatesandmixedcarbamateswithtunablewatersolubility AT zakariaatmani synthesisandcharacterizationofpolysaccharidecarbamatesandmixedcarbamateswithtunablewatersolubility AT lennarthendrikskodda synthesisandcharacterizationofpolysaccharidecarbamatesandmixedcarbamateswithtunablewatersolubility AT thomasheinze synthesisandcharacterizationofpolysaccharidecarbamatesandmixedcarbamateswithtunablewatersolubility |