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Title

Rhamnolipids functionalized with basic amino acids: Synthesis, aggregation behavior, antibacterial activity and biodegradation studies

AuthorsRamos da Silva, Antonio; Manresa, María Ángeles; Pinazo, Aurora; García, María Teresa; Pérez, Lourdes
KeywordsRhamnolipid production
Used cooking oil
Arginine and lysine derivatives
Physico-chemical properties
Antibacterial activity
Biodegradation
Issue Date1-Sep-2019
PublisherElsevier
CitationColloids and Surfaces - B - Biointerfaces 181: 234-243 (2019)
AbstractRhamnolipids have been intensively studied due to their remarkable properties; however, the biosynthesis of RLs cannot compete commercially with the production of synthetic surfactants. Here, novel cationic rhamnolipids (RLs) derivatives containing arginine and lysine were prepared for the first time using a straightforward synthetic procedure. The RLs used to prepare these new cationic derivatives were produced by Pseudomonas aeruginosa using waste frying oil as carbon source. It was found that the amino acid-based RLs form aggregates at very low concentrations, even below the CMC. Biodegradation studies indicate that these cationic RLs can be classified as readily biodegradable. Interestingly, the RL arginine conjugates exhibited notable DNA binding affinity and good antimicrobial activity against Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus, which increases the potential applications of these compounds. Consequently, the use of low-cost substrates and the added value of the final product constitute a more cost-effective rhamnolipid production.
Publisher version (URL)https://doi.org/10.1016/j.colsurfb.2019.05.037
URIhttp://hdl.handle.net/10261/183456
DOI10.1016/j.colsurfb.2019.05.037
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