Towards novel efficient monomeric surfactants based on serine, tyrosine and 4-hydroxyproline: synthesis and micellization properties

Tetrahedron

Volumn 65, Issue 21, 2009, Pages 4156-4164

  Silva, S Goreti ^a   Rodríguez Borges, J Enrique ^a   Marques, Eduardo F ^a   do Vale, M Luísa C ^a  

^a UNIVERSITY OF PORTO   (Portugal)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; ANIONIC SURFACTANT; HYDROXYPROLINE; SERINE; TYROSINE;

ARTICLE; DEPROTECTION REACTION; METHODOLOGY; MICELLIZATION; PRIORITY JOURNAL; SAPONIFICATION; SURFACE PROPERTY; SYNTHESIS;

EID: 64649097607     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.03.043     Document Type: Article

References (49)

1. Jönsson B., Lindman B., Holmberg K., and Kronberg B. Surfactants and Polymers in Aqueous Solution (1998), John Wiley Sons, England Chapter 1
2. Evans D.F., and Wennerström H. The Colloidal Domain: Where Physics, Chemistry, Biology and Technology Meet. 2nd ed (1999), Wiley-VCH, New York, NY
3. Holmberg K. Curr. Opin. Colloid Interface Sci. 6 (2001) 148-159
4. Van Hamme J.D., Singh A., and Ward O.P. Biotechnol. Adv. (2006) 604-620
5. Blunk D., Bierganns P., Bongartz N., Tessendorf R., and Stubenrauch C. New J. Chem. 30 (2006) 1705-1717
6. Morán M.C., Pinazo A., Pérez L., Clapés P., Angelet M., García M.T., Vinardell M.P., and Infante M.R. Green Chem. 6 (2004) 233-240
7. Roy S., Das D., Dasgupta A., Mitra R.N., and Das P.K. Langmuir 21 (2005) 10398-10404
8. von Rybinski W., and Hill K. Angew. Chem., Int. Ed. 37 (1998) 1328-1345
9. Kirk O., Pedersen F.D., and Fuglsang C.C. J. Surfactants Deterg. 1 (1998) 37-40
10. Johansson I., and Svensson M. Curr. Opin. Colloid Interface Sci. 6 (2001) 178-188
11. Hama I., Sasamoto H., Tamura T., Nakamura T., and Miura K. J. Surfact. Deterg. 1 (1998) 93-97
12. Claffey D.J., Meyer J.D., Beauvais R., Brandt T., Shefter E., Kroll D.J., Ruth J.A., and Manning M.C. Biochem. Cell Biol. 78 (2000) 59-65
13. Kondoh M., Furutani T., Azuma M., Ooshima H., and Kato J. Biosci. Biotechnol. Biochem. 61 (1997) 870-874
14. Rosa M., Penacho N., Simões S., Lima M.C.P., Lindman B., and Miguel M.G. Mol. Membr. Biol. 25 (2008) 23-34
15. Dias R.S., Lindman B., and Miguel M.G. J. Phys. Chem. B 106 (2002) 12600-12607
16. Dias R.S., Lindman B., and Miguel M.G. J. Phys. Chem. B 106 (2002) 12608-12612
17. Lewis J.G., Lin K.-Y., Kothavale A., Flanagan W.M., Matteucci M.D., DePrince R.B., Mook Jr. R.A., Hendren R.W., and Wagner R.W. Proc. Natl. Acad. Sci. U.S.A. 93 (1996) 3176-3181
18. Piera E., Comelles F., Erra P., and Infante M.R. J. Chem. Soc., Perkin Trans. 2 (1998) 335-342
19. Pérez L., Pinazo A., Garcia M.T., Morán M.C., and Infante M.R. New J. Chem. 28 (2004) 1326-1334
20. Macián M., Seguer J., Infante M.R., Selve C., and Vinardell M.P. Toxicology 106 (1996) 1-9
21. Sánchez L., Mitjans M., Infante M.R., García M.T., Manresa M.A., and Vinardell M.P. Amino Acids 32 (2007) 133-136
22. Diz M., Manresa A., Pinazo, Erra P.A., and Infante M.R. J. Chem. Soc., Perkin Trans. 2 (1994) 1871-1876
23. Yoshimura T., Sakato A., Tsuchiya K., Ohkubo T., Sakai H., Abe M., and Esumi K. J. Colloid Interface Sci. 308 (2007) 466-473
24. Brito R.O., Marques E.F., Gomes P., Falcão S., and Söderman O. J. Phys. Chem. B 110 (2006) 18158-18165
25. Rosa M., Miguel M.D., and Lindman B. J. Colloid Interface Sci. 312 (2007) 87-97
26. Preliminary results have been presented:
27. Vale, M. L. C.; Araújo, M. J. S. M. P.; Gomes, P. A. C.; Rodríguez-Borges, J. E.; Marques, E.; Silva, S. G.; Correia, C. Methodologies of Synthesis of Novel Surfactants Based on Amino Acids, 1st European Chemistry Congress, Budapest, Hungary, August, 2006;
28. Silva, S. G.; Oliveira, M.; Borges, J. E.; Marques, E. F.; Vale, M. L. Methodologies of Synthesis of Monomeric and Dimeric Surfactants Based on Amino Acids, 15th European Symposium on Organic Chemistry, Dublin, Ireland, July, 2007.
29. Gomes P., Araújo M.J., Marques E.F., Falcão S., and Brito R.O. Synth. Commun. 38 (2008) 2025-2036
30. Zana R., Benrraou M., and Rueff R. Langmuir 7 (1991) 1072-1075
31. Magid A.F.A., Carson K.G., Harris B.D., Maryanoff C.A., and Shah R.D. J. Org. Chem. 61 (1996) 3849-3862
32. Ramanjulu J.M., and Joullié M.M. Synth. Commun. 26 (1996) 1379-1384
33. Griffith W.P., Ley S.V., Whitcombe G.P., and White A.D. J. Chem. Soc., Chem. Commun. (1987) 1625-1627
34. Cho B.T., and Kang S.K. Tetrahedron 61 (2005) 5725-5734
35. Corey J.E., and Venkateswarlu A. J. Am. Chem. Soc. 94 (1972) 6190-6191
36. Larina L.I., Karnaukhova R.V., Nakhmanovich A.S., Shagun V.A., Ushakov P.E., and Lopyrev V.A. J. Mol. Struct. 604 (2002) 165-176
37. Shankar B.B., Yang D.Y., Girton S., and Ganguly A.K. Tetrahedron Lett. 39 (1998) 2447-2448
38. Wenschuh H., Beyermann M., Haber H., Seydel J.K., Krause E., and Bienert M. J. Org. Chem. 60 (1995) 405-410
39. Gaggini F., Porcheddu A., Reginato G., Rodriquez M., and Taddei M. J. Comb. Chem. 6 (2004) 805-810
40. Bodanszky M., and Bodanszky A. The Practice of Peptide Synthesis (1984), Springer, Berlin, Germany
41. García M.T., Ribosa I., Guindulain T., Sánchez-Leal J., and Vives-Rego J. Environ. Pollut. 111 (2001) 169-175
42. Mukherjee P., and Mysels K.J. Critical Micelle Concentrations of Aqueous Surfactant Solutions (1971), National Bureau of Standards, Washington, DC
43. Marques E.F., Brito R.O., Silva S.G., Rodríguez-Borges J.E., Vale M.L.d., Gomes P., Araújo M.J., and Söderman O. Langmuir (2008) 11009-11017
44. Kaler E.W., Murthy A.K., Rodriguez B.E., and Zasadzinski J.A.N. Science 245 (1989) 1371-1374
45. Marques E.F. Langmuir 16 (2000) 4798-4807
46. Fischer A., Hebrant M., and Tondre C. J. Colloid Interface Sci. 248 (2002) 163-168
47. Danoff E.J., Wang X., Tung S.H., Sinkov N.A., Kemme A.M., Raghavan S.R., and English D.S. Langmuir 23 (2007) 8965-8971
48. Kuo J.H.S., Chang C.H., Lin Y.L., and Wu C.J. Colloids Surf., B 64 (2008) 307-313
49. Brito, R. O.; Marques, E. F.; Silva, S. G.; Vale, M. L. d.; Gomes, P.; Araújo, M. J.; Rodríguez-Borges, J. E.; Infante, M. R.; García, M. T.; Ribosa, I.; Vinardell, M. P.; Mitjans, M. Colloids Surf., B, in press. doi:10.1016/j.colsurfb.2009.03.017