Non-conventional surfactants from amino acids and glycolipids: Structure, preparation and properties

Colloids and Surfaces A: Physicochemical and Engineering Aspects

Volumn 123-124, Issue , 1997, Pages 49-70

  Infante, Ma Rosa ^b   Pinazo, Aurora ^b   Seguer, Joan ^a,b  

^a Laboratorios Miret SA Polg Ind   (Spain)

^b DEPT OF ENVIRONMENTAL CHEMISTRY   (Spain)

Author keywords

Antimicrobials; Glycolipids; Lipoamino acids; Lipopeptides; Surfactants

Indexed keywords

AMINO ACIDS; ANTIBODIES; BIOCOMPATIBILITY; BIODEGRADATION; GLYCEROL; LIPIDS; MOLECULAR STRUCTURE; OLIGOMERS; POLYSACCHARIDES;

ANTIMICROBIALS; GLYCOLIPIDS; LIPOAMINO ACIDS; LIPOPEPTIDES; PHOSPHOLIPIDS;

SURFACE ACTIVE AGENTS;

AMINO ACID DERIVATIVE; GLYCOLIPID;

AMINO ACID ANALYSIS; ARTICLE; BIOTECHNOLOGY; CHEMICAL ANALYSIS; LIPID ANALYSIS; PRIORITY JOURNAL; STRUCTURE ANALYSIS; SURFACE PROPERTY;

EID: 0343036126     PISSN: 09277757     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0927-7757(96)03793-4     Document Type: Article

References (114)

1. H.J. Richtler and J. Kanaut, Proceedings 2nd World Surfactant Congress, Vol. 1, Paris, 1988, p. 3.
2. P. Latge, I. Rico, R. Garelli and A. Lattes, J. Dispersion Sci. Technol., 12(3,4) (1991) 227.
3. J.G. Riess, J. Greiner, M. Le Blanc, Y.S. Lin, A. Manfredi, S. Pace, C. Varescon and L. Zarif, Actual. Chim. Ther., 15 (1988) 247.
4. R. Moss, T.J. Lukas and R. Nahas, Tetrahedron Lett., 44 (1977) 3851.
5. K. Arim, A. Kakinuma and G. Tamura, Biochem. Biophys. Res. Commun., 31 (1968) 488.
6. D.G. Cooper, C.R. MacDonald, S.J.B. Duff and N. Kosaric, Appl. Environ. Microbiol., 42 (1981) 408.
7. M.M. Yakimov, K.N. Timmis, V. Wray and H.L. Frederickson, Appl. Environ. Microbiol., 61 (1995) 1706.
8. J.D. Spivak, Surfactant Science Series, Vol. 7, Anionic Surfactants II, Marcel Dekker, New York, 1976, Chapter 16.
9. T. Nakamiya, H. Mizuno, T. Meguno, H. Ryono and K. Takinami, J. Fermentn. Technol., 54 (1976) 368.
10. A.V. Prabhudesai and C.V. Viswanathan, Fette, Seifen, Anstrichm., 81 (1979) 194.
11. C. Selve, F. Hamdoune, L. Mansuy and M. Allouch, J. Chem. Res., (S) 22 (M) (1992) 401.
12. B. Gallot and A. Douy, U.S. Patent 4,600,526, 1986.
13. Y. Matsuzawa and T. Saito, Jpn. Patent 74,116,005.
14. M. Sisido, K. Akiyama and Y. Imanishi, Macromolecules, 17 (1984) 1773.
15. H. Hidaka, M. Murata and T. Onai, J. Chem. Soc., Chem. Commun., (1984) 562.
16. M. Takehara, Colloids Surfaces, 38 (1989) 149.
17. P. Than, in M.M. Rieger (Ed.), Surfactants in Cosmetics, Marcel Dekker, New York, 1985.
18. M. Bodarszky and A. Bodanszky, The Practice of Peptide Synthesis, Springer, Berlin, 1984, p. 21.
19. Ph. Sokol, J. Am. Oil Chem. Soc., 62 (1975) 101.
20. R.J. Sims and J.A. Fioriti, J. Am. Oil Chem. Soc., 52 (1975) 144.
21. E.B. Kester, U.S. Patent 2,463,779, 1949.
22. E. Jungermann, J.F. Gerecht and I.J. Krems, J. Am. Chem. Soc., 78 (1956) 172.
23. M. Takehara, I. Yoshimura, K. Takizawa and R. Yoshida, J. Am. Oil Chem. Soc., 49 (1972) 157.
24. W. Gryc, M. Dabrowska, B. Tomicka, D. Perkowska and G. Kupryszewski, Pol. J. Chem., 53 (1979) 1085.
25. aR. Juliá and J. García Domínguez, Proceedings XIV Jornadas CED, 1983, p. 263.
26. H. Yokota, K. Sagawa, C. Eguchi and M. Takehara, J. Am. Oil Chem. Soc., 62 (1985) 1716.
27. R. Geiger and W. Köning, Amine protecting groups, in E. Gross and J. Meienhofer (Eds.), The Peptides, Vol. 3, Academic Press, London, 1981, Chapter 1.
28. R. Yoshida, Babak, T. Saito and I. Yoshimura, J. Jpn. Oil Chem. Soc., 25 (1976) 404.
29. aR. Infante, J. Soc. Cosmet. Chem., 45 (1994) 53.
30. T. Hayakawa, Y. Fujiwara and J. Noguchi, Bull. Chem. Soc. Jpn., 40 (1967) 1205.
31. A. Paquet, U.S. Patent 4,126,628.
32. Y. Lapidot, S. Rappoport and Y. Wolman, J. Lipid Res., 8 (1967) 142.
33. M. Hiramoto, K. Okada, S. Nagai and H. Kawamoto, Chem. Pharm. Bull., 19 (1971) 1308.
34. aR. Infante and V. Moses, Int. J. Peptide. Protein Res., 43 (1994) 173.
35. J. Meienhofer, in E. Gross and J. Meienhofer (Eds.), The Peptides, Vol. 1, Academic Press, London, 1979, Chapter 4.
36. R.A. Boissonpaas, Helv. Chim. Acta, 34 (1951) 874.
37. J.R. Vaughan, J. Am. Chem. Soc., 73 (1951) 3547.
38. aR. Juliá and P. Erra, J. Am. Oil Chem. Soc., 66 (1989) 1835.
39. aR. Infante, J. Molinero and P. Erra, J. Am. Oil Chem. Soc., 69 (1992) 647.
40. aR. Infante, J. Chem. Soc., Perkin Trans., 2 (1994) 1871.
41. J.C. Sheehan and G.P. Hess, J. Am. Chem. Soc., 77 (1995) 1067.
42. aR. Juliá and M. Prats, Int. J. Cosmet. Sci., 6 (1984) 275.
43. aR. Juliá, J.J. García Domínguez and M. Robert, Fette, Seifen, Anstrichm., 88 (1986) 108.
44. aR. Infante, M. Allouch, L. Mansuy, P. Vinardell and C. Selve, New J. Chem., 18 (1994) 765.
45. aR. Infante, Langmuir, 12 (1996) 5296.
46. aR. Infante, L. Mansuy, J. Seguer and C. Selve, Proceedings XXV Jornadas CED, 1994, p. 443.
47. K. Takahashi, F. Tanaka and K. Motomura, Bull. Chem. Soc. Jpn., 57 (1984) 944.
48. aR. Juliá, J. Molinero and P. Erra, An. de Quim., 82 (1986) 413.
49. aR. Infante, A. Pes, A. Vílchez and C. Solans, An. Quim., 88 (1992) 542.
50. aA. Pes, Doctoral Thesis, U.B., 1992.
51. T. Kuwamura, Structure/performance relationships in surfactants, ACS Symp. Ser. 253, American Chemical Society, Washington, DC, 1984, 27-4752.
52. J. Seguer, Doctoral Thesis, U.B., 1993.
53. aR. Infante, J. Am. Oil Chem. Soc., 73 (1996) 79.
54. aP. Vinardell, Toxicology, 106 (1996) 1.
55. C. Selve, J.-C. Ravey, M.J. Stebe, E. El Mondjahid, E.M. Moummi and J.-J. Delpuech, Tetrahedron, 47 (1991) 411.
56. aR. Infante and C. Selve, J. Am. Oil Chem. Soc., 73 (1996) 87.
57. J.G. Heath and E. Arnett, J. Am. Chem. Soc., 114 (1992) 4500-4514.
58. K. Fukuda, Y. Shibasaki and H. Nakahara, J. Macromol. Sci. Chem., 15 (1981) 999.
59. aR. Juliá and J.J. Garcia Domínguez, Fette, Seifen, Anstrichm., 88 (1986) 108.
60. K. Sakamoto and M. Hatano, Bull. Chem. Soc. Jpn., 53 (1980) 339.
61. K. Sakamoto, R. Yoshida, M. Hatano and T. Tachibana, J. Am. Chem. Soc., 100 (1978) 6898.
62. aR. Infante and T. Warnheim, Prog. Colloid Polym. Sci., 79 (1989) 70.
63. aR. Infante, Prog. Colloid Polym. Sci., 81 (1990) 144.
64. aR. Infante, Colloids Surfaces, 79 (1993) 81.
65. aR. Infante and C. Solans, Adv. Mater., 4 (1992) 291.
66. Y. Sugimoto and S. Toyoshima, Antimicrob. Agents Chemother., 16 (1979) 329.
67. R.C. McKellar, A. Paquet and C-Y. Ma, Food Microbiol., 9 (1992) 67.
68. A. Cegielska, M. Dabrowska, B. Lammek, Z. Mackiewicz, A. Taylor and G. Kupryszewsky, Pol. J. Chem., 4 (1979) 324.
69. S.Y. Mhaskar, G. Lakshminarayana and L. Saisree, J. Am. Oil Chem. Soc., 70 (1992) 23.
70. Z.G. Wu, Ch.N. Ji and M.L. Shi, J. Am. Oil Chem. Soc., 70 (1992) 109.
71. L.S. Fosdick, J.C. Calandra, R.O. Blackwell and J.H. Burill, J. Dental Res., 32 (1953) 486.
72. Y. Kameda, E. Toyoura, S. Ohshima, M. Tsuji and C. Irie, J. Pharm. Soc. Jpn., 68 (1948) 143.
73. C. Madhosingh, A. Paquet, B.B. Migicovsky and W. Orr, J. Environ. Sci. Health, B13 (1978) 183.
74. A. Paquet and K. Rayman, Can. J. Microbiol., 33 (1987) 577.
75. W.B. Hugo, J. Appl. Bacteriol., 30 (1967) 17.
76. aR. Juliá, J. García Domínguez and M. Robert, Fette, Seifen, Anstrichm., 3 (1986) 108.
77. J. Ferguson, Proc. R. Soc. London, Ser. B., 127 (1939) 387.
78. aR. Infante, Int. J. Cosmet. Sci., 12 (1990) 13.
79. aR. Infante, Rev. Toxicol., 13 (1996) 9.
80. M. Robert, M. Mercadé, N. Castelar and J. Guinea, Proceedings XIV IFSCC Congreso, Vol. 1, Barcelona, 1986, p. 39.
81. P.S. Sastry, Adv. Lipid Res., 12 (1974) 251.
82. C.C. Sweely and B. Siddiqui, in M.J. Horrowitz and W. Pigman (Eds.), Glycoconjugates, Vol. 1, Academic Press, New York, 1987, pp. 459-540.
83. B.L. Slomiany, V.L.N. Murty, Y.K. Liau and A. Slomiany, Prog. Res. Lipids, 26 (1987) 29.
84. P.J. Quinn and W.P. Williams, Prog. Biophys. Mol. Biol., 24 (1978) 34, 109.
85. N. Shaw and D. Sted, J. Bacteriol., 107 (1971) 130.
86. M. Oshima and T. Yamakawa, Biochemistry, 13 (1974) 1140.
87. J.B. Ward, Microbiol. Rev., 45 (1981) 211.
88. M. Ishizuka and T. Yamakawa, in H. Wiegandt (Ed.), Glycolipids, New Comprehensive Biochemistry, Vol. 10, Elsevier and Academic Press, New York, pp. 101-197.
89. W. Curatolo, Biochim. Biophys. Acta, 906 (1987) 137.
90. J.F. Kennedy, Carbohydrate Chemistry: The Glycolipids and Gangliosides, pp. 196-219.
91. L. Six, K.P. Russ and M. Liefländer, Tetrahedron Lett., 24 (1983) 1229.
92. D.A. Mannock, R.N.H. Lewis and R.N. McElhanh, Chem. Phys. Lipids, 43 (1987) 11.
93. W. Königs and E. Knorr, Chem. Ber., 34 (1901) 957.
94. V. W. Wulff and G. Röhle, Angew. Chem., 86 (1974) 173.
95. R.R. Schmidt, Angew. Chem. Int. Ed. Engl., 25 (1986) 212.
96. H. Minamikawa, T. Murakami and M. Hato, Chem. Phys. Lipids, 72 (1994) 111.
97. J. Falbe (Ed.), Surfactants in Consumer Products. Theory, Technology and Application, pp. 100-104.
98. G.G. Shipley, Biochim. Biophys. Acta, 311 (1981) 531.
99. J. Seguer, H. Minamikawa and M. Hato, 48th Symposium on Colloid and Interface Chemistry, Sapporo, 1995.
100. H. Minamikawa and M. Hato, 48th Symposium on Colloid and Interface Chemistry, Sapporo, 1995.
101. A. Wielander, A. Christianson, L. Rilfors and G. Lindblom, Biochemistry, 19 (1980) 3650.
102. P.R. Cullis and B. De Kruijff, Biochim. Biophys. Acta, 559 (1979) 399.
103. W. Curatolo, Biochim. Biophys. Acta, 906 (1987) 111.
104. R. Koynova and M. Caffrey, Chem. Phys. Lipids, 69 (1994) 181.
105. P.L. Harris and E.R. Thornton, J. Am. Chem. Soc., 100 (1978) 6738-6745.
106. R.V. McDaniel and T.J. McIntosh, Biophysics, 49 (1986) 94-96.
107. F.J. Sharon and C.W.M. Grant, Biochim. Biophys. Acta, 507 (1978) 280-293.
108. I. Pascher, Biochim. Biophys. Acta, 455 (1976) 433.
109. S. Spiegel, R. Blumenthal, P.H. Fishman and J.S. Handler, Biochim. Biophys. Acta, 821 (1985) 310-318.
110. A. Surolia, B.K. Bachhawat and S.K. Podder, Nature, 257 (1975) 802-804.
111. W.R. Redwood and T.G. Polefteka, Biochim. Biophys. Acta, 455 (1976) 631.
112. J.S. Slama and R.R. Rando, Biochemistry, 19 (1980) 4595-4600.
113. W. Curalolo, Biochem. Biophys. Res. Commun., 106 (1982) 1340-1345.
114. R. Stahn, H. Schaefer, J. Schereiber and M. Brudel, J. Liposome Res., 5(1) (1995) 61-73.