Combined catalytic strategies in obtaining alanine-derived surfactants: Analysis of the products obtained and evaluation of biocidal activity
DOI:
https://doi.org/10.24215/3072905Xe001Keywords:
hydrogenolysis, alanine-derived surfactant, antimicrobial activityAbstract
This work presents the study of different alternatives for catalytic hydrogenolysis, along with the analysis of the products obtained in the synthesis of alanine-derived surfactants and the evaluation of their antimicrobial activity. The synthesis of these compounds involves a condensation reaction between an N-protected alanine derivative (Nα-carbobenzoxy-Ala) and alkylamines, catalyzed by papain (a plant endopeptidase), followed by hydrogenolysis of the product to remove the protecting group from the amino acid moiety. Two Pd-based catalysts supported on activated carbon were tested in the hydrogenolysis reactions.
Thin-layer chromatography (TLC) analysis revealed that the best results were achieved using a 10% (w/w) Pd/C catalyst after 4 h of reaction under 4 atm of H₂ pressure at 40 °C. Analyses by different two-dimensional NMR spectroscopy techniques and UPLC-MS demonstrated that the products formed were Nα-isopropyl-alanine amides. Under the selected conditions, the 2-propanol used as the reaction medium was able to react with the α-amino group of the amino acid moiety, displacing the Nα-carbobenzoxy protecting group. The resulting compounds exhibited both bacteriostatic and bactericidal activity against Staphylococcus aureus.
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Copyright (c) 2025 Patricia D. Grillo, Virginia Vetere, Maria Elisa Fait, Carlos R. Llerena Suster, Sergio Laurella, Susana R. Morcelle (Autor/a)
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