Semi-synthesis of N-alkyl-kappa-carrageenan derivatives and evaluation of their antibacterial activity
| Autor: | Fábio S. Murakami, Diogo R.B. Ducatti, Alan G. Gonçalves, Maria Eugênia R. Duarte, Edson Hipólito Júnior, Miguel D. Noseda |
|---|---|
| Rok vydání: | 2021 |
| Předmět: |
Staphylococcus aureus
Microbial Sensitivity Tests Carrageenan 010402 general chemistry medicine.disease_cause Polysaccharide 01 natural sciences Biochemistry Medicinal chemistry Reductive amination Analytical Chemistry chemistry.chemical_compound Carbohydrate Conformation Escherichia coli medicine Alkyl chemistry.chemical_classification 010405 organic chemistry Pseudomonas aeruginosa Chemistry Organic Chemistry General Medicine Anti-Bacterial Agents 0104 chemical sciences Antibacterial activity |
| Zdroj: | Carbohydrate Research. 499:108234 |
| ISSN: | 0008-6215 |
| DOI: | 10.1016/j.carres.2021.108234 |
| Popis: | In this article, we describe the semi-synthesis of N-alkyl-kappa-carrageenan derivatives and their antibacterial activity against Staphylococcus aureus (ATCC 6538), Escherichia coli (ATCC 8739), and Pseudomonas aeruginosa (ATCC 9027). Kappa-carrageenan was submitted to partial acid hydrolysis promoting the selective cleavage of α-glycosidic bonds involving 3,6-anhydro-α-D-Galp units, giving rise to reducing low-molecular weight polysaccharide fragments, which were reacted with alkylamines of varying chain lengths by reductive amination. The carrageenan derivatives were characterized by HPSEC-MALLS-RID and 1D and 2D 1H and 13C NMR spectroscopy. The antibacterial activity of N-alkyl-kappa-carrageenan derivatives was compared with N-alkyl-(1-deoxylactitol-1-yl)-amines using a microdilution test, which indicated that inhibitory activity was dependent on the degree of substitution by hydrophobic groups at the polysaccharide structure. Comparing the effect of different N-alkyl chains, those with longer chains showed higher activity. |
| Databáze: | OpenAIRE |
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