Lactose‐containing hydrogels for enzyme stabilization

Huang, Yongshun; Chai, Qinyuan; Warmin, Mary R.; Ayres, Neil

doi:10.1002/pola.28127

Cited by 7 publications

(5 citation statements)

References 51 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To sum up, we could demonstrate that our envisioned glycosyl acceptors bearing free hydroxyl groups at the 4-OH or the 6-OH position of the non-reducing end can be readily prepared. Suitable glycosyl donors were then synthesized as reported previously. , Using these trichloroacetimidates of cellobiose and maltose, 4a and 4b , oligomers with alternated configuration at the anomeric carbon were obtained after glycosylation with TMSOTf as catalyst (Scheme ). The tetrasaccharides contained both the cellobiose as well as the maltose building block and were connected via a 1 → 4 or a 1 → 6 glycosidic bond, respectively.…”

Section: Resultsmentioning

confidence: 99%

Block Copolysaccharides from Methylated and Acetylated Cellulose and Starch

Sommer

Zollfrank

2022

Biomacromolecules

View full text Add to dashboard Cite

All-glucose block copolysaccharides with alternated α- and β-configured blocks do not exist in nature. Such polysaccharides, and materials made thereof, might exhibit very interesting properties due to the different supramolecular structures of the two α- and β-configured blocks. This would be helical for starch and linear for cellulose in the case of a non-derivatized all-glucose polysaccharide. We propose a synthetic pathway for the preparation of methylated and acetylated building blocks of cellulose and amylose for the regioselective modification at the non-reducing and reducing end to act as glycosyl acceptors and donors, respectively. The glycosyl acceptors with the opposite α- or β-configured blocks were prepared by acid-catalyzed methanolysis of permethylated amylose as well as cellulose. The regioselectively modified glycosyl donors and acceptors were successfully used in the preparation of block copolysaccharides with an α(1 → 4)-configured and a β(1 → 4)-configured oligo- or polysaccharide block, respectively.

show abstract

Section: Resultsmentioning

confidence: 99%

Block Copolysaccharides from Methylated and Acetylated Cellulose and Starch

Sommer

Zollfrank

2022

Biomacromolecules

View full text Add to dashboard Cite

show abstract

“…Methacrylates are known for their ability to self-initiate under irradiation. , The facile chemistry to access lactose-containing polymers in this experiment makes it ideal for a teaching laboratory setting. Previous works on lactose-containing polymers typically involved multistep syntheses and the need for protecting groups. − …”

Section: Introductionmentioning

confidence: 99%

Synthesis and Characterization of Biobased Lactose Hydrogels: A Teaching Experiment on Sustainable Polymers and Waste Biomass Valorization

Buenaflor,

Hillmyer,

Wentzel

et al. 2023

J. Chem. Educ.

View full text Add to dashboard Cite

Hydrogels are soft water-rich materials with physical properties that can be easily tuned by modifying their network structure. For instance, increasing or decreasing the cross-linking density has a profound effect on their water absorption capabilities and mechanical strength. These physical changes are showcased in a new experiment for organic chemistry and polymer science teaching laboratories based on the practical green synthesis and characterization of lactose methacrylate derived hydrogels. Lactose, a disaccharide derived from dairy waste byproducts, is functionalized with photoreactive methacrylate groups using methacrylic anhydride. The resulting mixture is subsequently photoirradiated to generate a cross-linked hydrogel. Structure–property relationships are assessed through comparative studies of three hydrogels of varying compositions. Compression tests and swelling studies in different aqueous environments offer a guided-inquiry experience. Students determine a relationship between cross-linking density and the physical properties of the hydrogels. This experiment highlights the valorization of biomass and multiple green chemistry principles including use of renewable feedstocks, atom economy, energy efficiency, waste prevention, and water as a benign solvent. Learning outcomes for an organic chemistry laboratory course include introduction to disaccharide and cross-linked polymer structures, observable physical change dependency with cross-linking density, and laboratory methods for evaluating water absorption capacities. Objectives aligned with a polymer course are incorporating mechanical compression instrumentation, mechanistic understanding of light-induced free radical polymerizations, and an appreciation for the application of hydrogels to commercial products. Overall, the translation of a current literature publication to an inexpensive and versatile experiment engages students in a modern example of sustainable polymer chemistry.

show abstract

“…26 Our lab has studied the effects of incorporating sugar units into polyurethane and polyurea backbones. [27][28][29][30][31][32][33][34] For instance, polyureas with sulfated sugars (glucose, lactose, mannose, and glucosamine) showed effective anticoagulant properties in prolonged blood clotting time assays. 31 The non-sulfated, hydroxylated polymers demonstrated decreased platelet adhesion and water contact angle measurements, indicating the biocompatibility and hydrophilicity of the sugar functionalized polyureas.…”

Section: Introductionmentioning

confidence: 99%

“…33 In other work from our group, lactose-containing hydrogels were synthesized through radical polymerization of N -(2-lactosylethyl)acrylamide and demonstrated potential applications in preserving enzyme activity. 34 However, up until now, the sugar monomers used throughout our research required lengthy, complicated, and costly synthetic procedures.…”

Section: Introductionmentioning

confidence: 99%