Synthesis and physicochemical studies of methyl-12-[1′-β-D-lactosyl]-octadec-9-ene-1-oate: A novel biosurfactant analog

Journal of Surfactants and Detergents

Volumn 2, Issue 4, 1999, Pages 531-538

  Kanjilal, Sanjit ^a   Maiti, S ^a   Kaimal, T N B ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aggregation number; Biosurfactant; Critical micelle concentration; Fluorescence probing technique; Free energy of adsorption; Free energy of micellization; Maximal densities; Minimal area per molecule; Pyrene; Surface tension

Indexed keywords

EID: 18244385746     PISSN: 10973958     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11743-999-0102-7     Document Type: Article

References (33)

1. Georgiou, G., S.-C. Lin, and M.M. Sharma, Surface Active Compounds from Microorganisms, Biotechnology 10:60 (1992).
2. Ishigami, Y., Biosurfactants Face Increasing Interest, INFORM 4:1156 (1993).
3. Ishigami, Y., and S. Suzuki, Development of Biochemicals - Functionalization of Biosurfactants and Natural Dyes, Prog. Org. Coatings 31:51 (1997).
4. Kosaric, N., W.L. Cairns, and N.C.C. Gray, Structure and Properties of Biosurfactant, in Biosurfactants and Biotechnology, Surfactant Science Series, Marcel Dekker Inc., New York, 1987, Vol. 25, p. 21.
5. Hisatsuka, K., T. Nakahara, N. Sano, and K. Yamada, Formation of Rhamnolipid by Pseudomonas aeruginosa and Its Function in Hydrocarbon Fermentation, Agr. Biol. Chem. 33:686 (1971).
6. Ristau, E., and F. Wagner, Formation of Novel Trehalose Tetraesters from Rhodococcus erythropolis Under Growth Limited Conditions, Biotechnol. Lett. 5:95 (1983).
7. Kakinuma, A., M. Hori, H. Sugino, M. Yoshido, M. Isono, G. Tamura, and K. Arima, Determination of the Location of Lactone Ring in Surfactin, Agr. Biol. Chem. 33:1523 (1969).
8. Gorin, P.A.J., J.F.T. Spencer, and A.P. Tulloch, Hydroxy Fatty Acid Glycosides of Sophorose from Torulopsis magnolide, Can. J. Chem. 39:846 (1961).
9. Brennan, P.J., D.P. Lehane, and D.W. Thomas, Acylglucoses of the Corynebacteria and Mycobacteria, Eur. J. Biochem. 13:117 (1970).
10. Ishigami, Y., Y. Gama, H. Nagahora, M. Yamaguchi, H. Nakagara, and T. Kamata, The pH Sensitive Conversion of Molecular Aggregates of Rhamnolipid Biosurfactant, Chem. Lett.:763 (1987).
11. Dupuy, C., X. Auvray, and C. Petipas, Anomeric Effects on the Structure of Micelles of Alkyl Maltosides in Water, Langmuir 13:3965 (1997).
12. Balzer, D., Cloud Point Phenomena in the Phase Behavior of Alkyl Polyglucosides in Water, Ibid. 9:3375 (1993).
13. Drummond, C.J., G.G. Warr, F. Grieser, B.W. Ninham, and D.F. Evans, Surface Properties and Micellar Interfacial Microenvironment of n-Dodecyl-β-D-maltoside, J. Phys. Chem. 89:2103 (1985).
14. Warr, G.G., C.J. Drummond, F. Grieser, B.W. Ninhan, and D.F. Evans, Aqueous Solution Properties of Nonionic n-Dodecyl-β-D-maltoside Micelles, Ibid. 90:4581 (1986).
15. Turro, N.J., B.H. Baretz, and P.-L. Kuo, Photoluminescence Probes for the Investigation of Interactions Between Sodium Dodecyl Sulfate and Water Soluble Polymers, Macromolecules 27:1321 (1984).
16. Kalyansundaran, K., and J.K. Thomas, Environmental Effects on Vibronic Band Intensities in Pyrene Monomer Fluorescence and Their Application in Studies of Micellar System, J. Am. Chem. Soc. 99:2039 (1977).
17. Turro, N.J., and P.-L. Kuo, Fluorescence Probe for Aqueous Solution of Nonionic Micelles, Langmuir 1:170 (1985).
18. Stam, J.V., N. Wittouck, M. Almgren, F.C.D. Schryver, and M.D.G. Miguel, The Role of Polymer Flexibility on the Interaction with Surfactant Micelles: Poly (vinyl alcohol) and Sodium Dodecyl Sulphate Aqueous Micelle Interactions Studied by Dynamic Fluorescence Quenching, Can. J. Chem. 73:1765 (1995).
19. C.S. Hudson, and J.M. Johnson, Isomeric Octaacetates of Lactose, J. Am. Chem. Soc. 37:1270 (1915).
20. Bochkov, A.F., and G.E. Zaikov, Formation of O-Glycosidic Bond: General Discussion, in Chemistry of the O-Glycosic Bond: Formation & Cleavage, USSR Academy of Science, Moscow, 1979, p. 16.
21. De Grip, W.J., and P.H.M. Bovee-Geurts, Synthesis and Properties of Alkyl Glucosides with Mild Detergent Action: Improved Synthesis and Purification of β-1-Octyl-, -Nonyl-, and -Decyl-glucose. Synthesis of β-1-Undecyl Glucose and β-1-Dodecyl Maltose, Chem. Phys. Lipids 23:321 (1979).
22. Ishigami, Y., Y. Gama, F. Ishii, and Y.K. Choi, Colloid Chemical Effect of Polar Head Moieties of a Rhamnolipid-Type Biosurfactant, Langmuir 9:1634 (1993).
23. Zhang, L., P. Somasundaran, and C. Maltesh, Electrolyte Effects on the Surface Tension and Micellization of n-Dodecyl-β-D-maltoside Solution, Ibid. 12:2371 (1996).
24. Böcker, T., and J. Thiem, Synthese und Eigenschaften von Kohlenhydrattensiden, Tenside 26:318 (1989).
25. Wilhelm, M., C.L. Zhao, Y. Wang, R.L. Xu, M.A. Winnik, J.L. Mura, G. Riess, and M.D. Croucher, Poly (styrene-ethylene oxide) Block Copolymer Micelle Formation in Water: A Fluorescence Probe Study, Macromolecules 24:1033 (1991).
26. xOH, in Aqueous Solution, J. Phys. Chem. 86:541 (1982).
27. Dahanayake, M., A.W. Cohen, and M.J. Rosen, Relationship of Structure to Properties of Surfactants. 13. Surface and Thermodynamic Properties of Some Oxyethylenated Sulfates and Sulfonates, Ibid. 90:2413 (1986).
28. Turro, N.J., and A. Yekta, Luminescent Probes for Detergent Solutions. A Simple Procedure for the Determination of the Mean Aggregation Number of Micelles, J. Am. Chem. Soc. 100: 5951 (1978).
29. Komaromy-Hiller, G., N. Calkin, and R.V. Wandruszka, Changes in Polarity and Aggregation Number upon Clouding of a Nonionic Detergent: Effect of Ionic Surfactants and Sodium Chloride, Langmuir 12:916 (1996).
30. Turro, N.J., M. Gratzel, and A.M. Braun, Photophysical and Photochemical Processes in Micellar Systems, Angew. Chem. Int. Edn. Engl. 19:675 (1980).
31. Pastor, O., E. Junquera, and E. Aicart, Hydration and Micellization Processes of n-Octyl-β-D-glucopyranoside in Aqueous Solution. A Thermodynamic and Fluorimetric Study in the Absence and Presence of Salts, Langmuir 14:2950 (1998).
32. Zana, R., Luminescence Probing Methods, in Surfactant Solutions. New Methods of Investigation, edited by R. Zana, Marcel Dekker Inc., New York, 1987, Vol. 22, p. 242.
33. Wieslander, Å., J. Ulmius, G. Lindblom, and K. Fontell, Water Binding and Phase Structures for Different Acholeplasma laidlaw II Membrane Lipids Studied by Deuteron Nuclear Magnetic Resonance and X-Ray Diffraction, Biochim. Biophys. Acta 512:241 (1978).