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Journals / Journal of Physical Chemistry and Functional Materials / 2026 / Volume: 9 Issue: 1

Enhancing Enzymatic Synthesis of Rhamnolipidic Biosurfactant. Effect of the Polar Head.

Bidjou-Haiour Chahra(UBMA)0000-0003-3682-0871
Loulou Fatma(UBMA)0000-0003-2262-9031
Pages
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Publication Date
2026-06-29
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AI Summary & Key Takeaways

AI Insight
⚡ TL;DR(Too Long; Didn't Read)

Exploring conformational space by folding molecules allows visualization and prediction of the shape of the surfactant monomer in molecular aggregates.

📌 3 Key Takeaways

🎯
Objective & Hypothesis:Process optimization of rhamnolipidic biosurfactant was carried out by studying the factors affecting the activity of the lipase such as the effect of the solvent and the ratio between the reagents.
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Key Findings & Data:Highest activity was found in acetone up to 95% in the esterification between L-rhamnose and palmitic acid using Candida antartica lipase B.
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Conclusion & Impact:Exploring conformational space by folding molecules allows visualization and prediction of the shape of the surfactant monomer in molecular aggregates.
🔬Design:Modeling & Simulation
📍Scope:Comprehensive Sample
⚙️Variables:Enzymatic catalysis · Sugar ester · Surface properties

Abstract

Process optimization of rhamnolipidic biosurfactant was carried out by studying the factors affecting the activity of the lipase such as the effect of the solvent and the ratio between the reagents. Highest activity was found in acetone up to 95% in the esterification between L-rhamnose and palmitic acid using Candida antartica lipase B. Moreover, surface-active properties of rhamnose palmitate and xylose palmitate were investigated in a comparative study in order to determine the influence of the polar head on the surfactant properties. Exploring conformational space by folding molecules allows visualization and prediction of the shape of the surfactant monomer in molecular aggregates.

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Cite This Article

Chahra, B., Fatma, L. (2026). Enhancing Enzymatic Synthesis of Rhamnolipidic Biosurfactant. Effect of the Polar Head.. Journal of Physical Chemistry and Functional Materials, Volume: 9 Issue: 1. https://doi.org/10.54565/jphcfum.1908027

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References (39)

  1. Sudarsanam, P., Mallesham, B., Prasad, A. N., Reddy, P. S., and Reddy, B. M., (2013). Synthesis of bio–additive fuels from acetalization of glycerol with benzaldehyde over molybdenum promoted green solid acid catalysts. Fuel Processing Technology. 106, 539-545. https://doi.org/10.1016/j.fuproc.2012.09.025
  2. Yang, Z., & Huang, Z. L, (2012). Enzymatic synthesis of sugar fatty acid esters in ionic liquids. Catalysis Science & Technology. 2(9), 1767-1775. https://doi.org/10.1039/C2CY20109G
  3. Ren, K., Chen, G., Zhang, Z., Long, Z., Zhou, B., Han, W., and Lin, Q, (2025). Enzymatic synthesis of some sugar-lauric acid esters by lipase from Candida antarctica and their functionalities as emulsifiers and antibacterial agents. Food Chemistry:X.27,102383. https://doi.org/10.1016/j.fochx.2025.102383
  4. Stergiou, P.Y., Foukis, A., Filippou, M., Koukouritaki, M., Parapouli, M., Theodorou, L.G., Hatziloukas, E., Afendra, A., Pandey, A. and Papamichael, E.M., (2013). Advances in lipase-catalyzed esterification reactions. Biotechnology advances. 31(8), 1846-1859. https://doi.org/10.1016/j.biotechadv.2013.08.006
  5. Kumar, A., Dhar, K., Kanwar, S.S., Arora, P.K., (2016). Lipase catalysis in organic solvents: advantages and applications. Biol. Proced. Online. 18, 1–11. https://doi.org/10.1186/s12575-016-0033-2
  6. Kennedy, J. F., Kumar, H., Panesar, P. S., Marwaha, S. S., Goyal, R., Parmar, A., and Kaur, S., (2006). Enzyme‐catalyzed regioselective synthesis of sugar esters and related compounds. Journal of Chemical Technology & Biotechnology: International Research in Process, Environmental & Clean Technology. 6, 866-876. https://doi.org/10.1002/jctb.1473
  7. Contesini, F. J., Lopes, D. B., Macedo, G. A., da Graça Nascimento, M., and de Oliveira Carvalho, P., (2010). Aspergillus sp. lipase: potential biocatalyst for industrial use. Journal of Molecular Catalysis B: Enzymatic. 67,163-71. https://doi.org/10.1016/j.molcatb.2010.07.021
  8. Plou, F. J., Cruces, M. A., Ferrer, M., Fuentes, G., Pastor, E., Bernabé, M., Christensen, M., Comelles, F., Parra, J.L. and Ballesteros, A., (2002). Enzymatic acylation of di-and trisaccharides with fatty acids: choosing the appropriate enzyme, support and solvent. Journal of Biotechnology. 96, 55-66. https://doi.org/10.1016/S0168-1656(02)00037-8
  9. Kawaguti, H. Y., Manrich, E., and Sato, H. H., (2006). Production of isomaltulose using Erwinia sp. D12 cells: culture medium optimization and cell immobilization in alginate. Biochemical engineering journal. 29(3), 270-277. https://doi.org/10.1016/j.bej.2006.01.006
  10. Ferrer, M., Cruces, M. A., Plou, F.J., Pastor, E., Fuentes, G., Bernabé, M., Parra, J.L. and Ballesteros, A., (2000). Chemical versus enzymatic catalysis for the regioselective synthesis of sucrose esters of fatty acids. Studies in Surface Science and Catalysis. 130, 509-514. https://doi.org1/0.1016/S0167-2991(00)81008-3
  11. Neta, N.S., Teixeira, J.A. and Rodrigues, L.R., (2015). Sugar ester surfactants: Enzymatic synthesis and applications in food industry. Critical Reviews in Food Science and Nutrition. 55(5), 595-610. https://doi.org/10.1080/10408398.2012.667461
  12. Klai, N., Bidjou-Haiour, C. and Bouquillon, S., (2015). D-Xylose-based surfactants: Synthesis, characterization and molecular modeling studies. Comptes Rendu. Chimie. 18(6), 599- 606. https://doi.org/10.1016/j.crci.2014.11.007
  13. Loulou, F., and Bidjou-Haiour, C., (2023). Lipase catalyzed synthesis of D-xylose-based biosurfactants and their surface properties. Current Organic Chemistry. 27(15), 1357-1364. https://doi.org/10.2174/0113852728269186231009103910
  14. Landge, D. D., Girase, C. D., and Kulkarni, R. D., (2025). Renewable green synthesis routes for alkylpolyglucoside surfactant and its application. Journal of Molecular Liquids. 128309. https://doi.org/10.1016/j.molliq.2025.128309
  15. Vainikka, P., Edler, K. J. (2026). Surfactant self-assembly and micelle elongation in reline: structural basis and driving forces. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences, 384(2316). https://doi.org/10.1098/rsta.2024.0316
  16. Vyas, J., Bhalani, D., Dalsaniya, G., Kumar, S., Aswal, V. K., Pillai, S. A. (2026). Carbohydrate-Surfactant Interplay: Structural Effects of Saccharides on Micellar Behavior of Kolliphor® EL and Kolliphor® HS15. Food Hydrocolloids for Health, 100274. https://doi.org/10.1016/j.fhfh.2026.100274
  17. Nicholls, A., McGaughey, G. B., Sheridan, R. P., Good, A. C., Warren, G., Mathieu, M., Kelley, B. (2010). Molecular shape and medicinal chemistry: a perspective. Journal of medicinal chemistry, 53(10), 3862-3886. https://doi.org/10.1021/jm900818s
  18. Ron, E.Z., Rosenberg, E., (2001). Natural roles of biosurfactants: Minireview. Environmental microbiology. 3(4), 229-236. https://doi.org/10.1046/j.1462-2920.2001.00190.x
  19. Schramm, L.L., Stasiuk, E.N., and Marangoni, D.G., (2003). Surfactants and their applications. Annual Reports Section "C" (Physical Chemistry). 99, 3-48. https://doi.org/10.1039/B208499F
  20. Ferrer, M., Soliveri, J., Plou, F.J., López-Cortés, N., Reyes-Duarte, D., Christensen, M., Copa-Patiño, J.L. and Ballesteros, A., (2005). Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties. Enzyme and Microbial Technology. 36(4), 391-398. https://doi.org/10.1016/j.enzmictec.2004.02.009
  21. Bidjou-Haiour, C. and Klai, N., (2013). Lipase catalyzed synthesis of fatty acid xylose esters and their surfactant properties. Asian Journal of Chemistry. 25(8), 4347-4350. https://doi.org/10.14233/ajchem.2013.13973
  22. Rezgui, N., (2022). Les esters de sucres. Synthèse et optimisation. PhD Thesis, UBMA, Algeria. Available from: https://biblio.univ-annaba.dz/wp-content/uploads/2023/06/These-Rezgui-Nacer.pdf
  23. Secundo, F., Carrea, G., Tarabiono, C., Gatti-Lafranconi, P., Brocca, S., Lotti, M., Jaeger, K.E., Puls, M. and Eggert, T., (2006). The lid is a structural and functional determinant of lipase activity and selectivity. Journal of Molecular catalysis B: enzymatic. 39(1-4), 166-170. https://doi.org/10.1016/j.molcatb.2006.01.018
  24. Kornblatt, J. A., and M. J. Kornblatt., (2002). Water as it applies to the function of enzymes. International review of cytology. 215, 49-73. https://doi.org/10.1016/S0074-7696(02)15005-4Get rights and content
  25. Yang, G., Wu, J., Xu, G., Yang, L., (2009). Enantioselective resolution of 2-(1-hydroxy-3-butenyl) methylfuran by immobilized lipase. Applied microbiology and biotechnology. 81(5), 847-853. https://doi.org/10.1007/s00253-008-1713-x
  26. Loulou, F., Rezgui, N., and Bidjou-Haiour, C., (2019). Preparation and Evaluation of Xylose Palmitate Ester Using Candida antarctica Lipase B as A Reusable Biocatalyst. Egyptian Journal of Chemistry. 62(3), 469-474. https://doi.org/10.21608/ejchem.2018.5160.1458
  27. Kumar, V.V., (1991). Complementary molecular shapes and additivity of the packing parameter of lipids. Proceedings of the National Academy of Sciences. 88(2), 444-448. https://doi.org/10.1073/pnas.88.2.44
  28. Israelachvili, J.N., (1992). Surface and Intermolecular Forces. Academic Press: New York.
  29. Argudo, P.G., Spitzer, L., Jerome, F., Cramail, H., Camacho, L. and Lecommandoux, S., (2022). Design and self-assembly of sugar-based amphiphiles: spherical to cylindrical micelles. Langmuir. 38(24), 7535-7544. https://doi.org/10.1021/acs.langmuir.2c00579
  30. Badel, A., Mornon, J.P., Hazout, S., (1992). Searching for geometric molecular shape complementarity using bidimensional surface profiles. Journal of Molecular Graphics. 10(4), 205-211. https://doi.org/10.1016/0263-7855(92)80069-P.
  31. Kumar, A., Zhang, K.Y., (2018). Advances in the development of shape similarity methods and their application in drug discovery. Frontiers in chemistry. 6, 1-21. https://doi.org/10.3389/fchem.2018.00315
  32. Martı́nez-Landeira, P., López-Fontán, J.L., Ruso, J.M., Prieto, G. and Sarmiento, F., (2003). Surface behaviour of C5, C6, C7 and C8 lecithins at the aqueous solution/air interface. Colloids and Surfaces A: Physicochemical and Engineering Aspects. 216(1-3), 91-96. https://doi.org/10.1016/S0927-7757(02)00504-6
  33. Hanwell, M. D., Curtis, D. E., Lonie, D. C., Vandermeersch, T., Zurek, E., and Hutchison, G. R., (2012). Avogadro: an advanced semantic chemical editor, visualization, and analysis platform. Journal of cheminformatics. 4(1), 17. http://www.jcheminf.com/content/4/1/17
  34. Greenspoon, N., Wachtel, E. (1991). Reverse micelles as a model system for carbohydrate binding. Journal of the American Chemical Society, 113(19), 7233-7236. https://doi.org/10.1021/ja00019a021
  35. Diat, O.,Bauduin, P. (2026). Amphiphiles in organic solvents: Reverse self-assembly. Current Opinion in Colloid & Interface Science, 102020. https://doi.org/10.1016/j.cocis.2026.102020
  36. Sekhon, B.S., (2013). Surfactants: Pharmaceutical and Medicinal Aspects. Journal of PharmaceuticalTechnology, Research and Management. 1, 43–68. https://doi.org/10.15415/jptrm.2013.11004
  37. Israelachvili, N., (2022). Surface forces, in: The Handbook of Surface maging and Visualization, CRC Press, 793–816. https://doi.org/10.1201/9780367811815
  38. Ren, K., Chen, G., Zhang, Z., Long, Z., Zhou, B., Han, W., and Lin, Q, (2025). Enzymatic synthesis of some sugar-lauric acid esters by lipase from Candida antarctica and their functionalities as emulsifiers and antibacterial agents. Food Chemistry:X.27,102383. https://doi.org/10.1016/j.fochx.2025.102383
  39. Schramm, L.L., Stasiuk, E.N., and Marangoni, D.G., (2003). Surfactants and their applications. Annual Reports Section "C" (Physical Chemistry). 99, 3-48. https://doi.org/10.1039/B208499F