Chemo-enzymatic Synthesis and Properties of Novel Optically Active Cationics Containing Carbonate Linkages

Journal of Oleo Science

Volumn 60, Issue 4, 2011, Pages 185-195

  Banno, Taisuke ^a   Kawada, Kazuo ^b   Matsumura, Shuichi ^a  

^a KEIO UNIVERSITY   (Japan)

^b KITASATO UNIVERSITY   (Japan)

Author keywords

Biodegradability; Carbonate linkage; Lipase; Quaternary ammonium type cationics; Stereochemistry

Indexed keywords

BIODEGRADABILITY; LIPASES; STEREOCHEMISTRY; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

ANTI-MICROBIAL ACTIVITY; CATIONICS; CHEMO-ENZYMATIC SYNTHESIS; DIPHENYL CARBONATE; ENANTIOSELECTIVE HYDROLYSIS; EXCHANGE REACTION; HYDROLYTIC STABILITY; SURFACTANT PROPERTIES;

CARBONATION;

EID: 79953070444     PISSN: 13458957     EISSN: 13473352     Source Type: Journal    
DOI: 10.5650/jos.60.185     Document Type: Article

References (33)

1. Morán, C; Pinazo, A.; Pérez, L.; Clapés, P.; Angelet, M.; García, T.; Vinardell, P.; Infante, R. Green amino acid-based surfactants. Green Chem. 6, 233-240 (2004).
2. Goursaud, F.; Berchel, M.; Guilbot, J.; Legros, N.; Le-miègre, L.; Marcilloux, J.; Plusquellec, D.; Benvegnu, T. Glycine betaine as a renewable raw material to greener new cationic surfactants. Green Chem. 10, 310-320(2008).
3. Okada, Y.; Banno, T.; Toshima, K.; Matsumura, S. Synthesis and properties of polycarboxylate-type green surfactants with S- or N -linkages. J. Oleo Sci. 58, 519-528(2009).
4. Fernández, P.; Valls, M.; Bayona, J. M.; Albalgés, J. Occurrence of cationic surfactants and related products in urban coastal environments. Environ. Sci. Technol. 25, 547-550(1991).
5. Tatsumi, T.; Zhang, W.; Kida, T.; Nakatsuji, Y.; Ono, D.; Takeda, T.; Ikeda, I. Novel hydrolyzable and biodegradable cationic gemini surfactants: 1,3-bis [(acyloxyalkyl) dimethylammonio] -2-hydroxy-propane dichloride. J. Surfact. Deterg. 3, 167-172(2000).
6. Tehrani-Bagha, A. R.; Oskarsson, H.; van Ginkel, C. G.; Holmberg, K. Cationic ester-containing gemini surfactants: chemical hydrolysis and biodegradation. J. Colloid Interface Sci. 312, 444-452 (2007).
7. Stjerndahl, M.; Holmberg, K. Hydrolyzable nonionic surfactants: stability and physicochemical properties of surfactants containing carbonate, ester, and amide bonds. J. Colloid Interface Sci. 291, 570-576(2005).
8. Banno, T.; Toshima, K.; Kawada, K.; Matsumura, S. Synthesis and properties of biodegradable and chemically recyclable cationic surfactants containing carbonate linkages. J. Oleo Sci. 56, 493-499 (2007).
9. Banno, T.; Toshima, K.; Kawada, K.; Matsumura, S. Synthesis and properties of gemini-type cationic surfactants containing carbonate linkages in the linker moiety directed toward green and sustainable chemistry. J. Surfact. Deterg. 12, 249-259 (2009).
10. Banno, T.; Kawada, K.; Matsumura, S. Creation of novel green and sustainable gemini-type cationics containing carbonate linkages. J. Surfact. Deterg. 13, 387-398(2010).
11. Boyd, B. J.; Krodkiewska, I.; Drummond, C. J.; Grieser, F. Chiral glucose-derived surfactants: the effect of stereochemistry on thermotropic and lyotropic phase behavior. Langmuir 18, 597-601 (2002).
12. Harvey, N. G.; Mirajovsky, D.; Rode, P. L.; Verbiar, R.; Arnett, E. M. Molecular recognition in chiral monolayers of stearoylserine methyl Ester. J. Am. Chem. Soc 111, 1115-1122(1989).
13. Zhang, Y. J.; Song, Y.; Zhao, Y; Li, T. J.; Jiang, L.; Zhu, D. Chiral discrimination in Langmuir monolayers of N-ac-yl glutamic acids inferred from π-A measurements and atomic force microscopy. Langmuir 17, 1317-1320 (2001).
14. Ambrost, M.; Nostro, P. L.; Fratini, E.; Giustini, L.; Nin-ham, B. W.; Baglioni, P. Effect of headgroup chirality in nanoassemblies. Part 1. Self-assembly of D-isoascorbic acid derivatives in water. J. Phys. Chem. B. 113, 1404-1412(2009).
15. Aisaka, T.; Oida, T.; Kawase, T. A novel synthesis of succinic acid type gemini surfactant by the functional group interconversion of corynomicolic acid. J. Oleo Sci. 56, 633-644(2007).
16. Faustino, C. M. C; Calado, A. R. T.; Garcia-Rio, L. Gemini surfactant-protein interactions: effect of pH, temperature, and surfactant stereochemistry. Biomac-romolecules 10, 2508-2514(2009).
17. Cornelissen, J. J. L. M.; Rowan, A. E.; Nolte, R. J. M.; Sommerdijk, N. A. J. M. Chiral architectures from macromolecular building blocks. Chem. Rev. 101, 4039-4070(2001).
18. Schmid, R. D.; Verger, R. Lipases: interfacial enzymes with attractive applications. Angew. Chem. Int. Ed. 37, 1608-1633(1998).
19. Ghanem, A.; Aboul-Enein, H. Y Lipase-mediated chiral resolution of racemates in organic solvents. Tetrahedron Asymmetry 15, 3331-3351 (2004).
20. Hull, J. D.; Scheinmann, F.; Turner, N. J. Synthesis of optically active methadones, LAAM and bufuralol by lipase-catalyzed acylations. Tetrahedron Asymmetry 14, 567-576(2003).
21. Chan, M. M. L.; Robinson, J. B. Stereoisomeric lactoyl-(3-methylcholine iodides. Interaction with cholinester-ase and acetylcholinesterase. J. Med. Chem. 17, 1057-1060(1974).
22. Molecular Operating Environment (MOE) Version 2009.10, software available from Chemical Computing Group Inc., 1010 Sherbrooke Street West, Suite 910, Montreal, Canada H3A 2R7.
23. Berman, H. M.; Westbrook, J.; Feng, Z.; Gilliland, G.; Bhat, T. N.; Weissig, H.; Shindyalov, I. N.; Bourne, P. E. The protein data bank. Nucleic Acids Res. 28, 235-242 (2000).
24. Esumi, K.; Taguma, K; Koide, Y Aqueous properties of multichain quaternary cationic surfactants. Langmuir 12, 4039-4041 (1996).
25. Bristline Jr, R. G.; Maurer, E. W.; Smith, F. D.; Linfield, W. M. Fatty acid amides and anilides, syntheses and antimicrobial properties. J. Am. Oil Chem. Soc. 57, 98-103(1980).
26. OECD guidelines for testing of chemicals, 301C, modified MITI test, Organization for Economic Cooperation and Development (OECD), Paris (1981).
27. Kazlauskas, R. J.; Weissfloch, A. N. E. A structure-based rationalization of the enantiopreference of sub-tilisin toward secondary alcohols and isosteric primary amines. J. Mol. Catal. B: Enzymatic 3, 65-72 (1997).
28. van Buijtenen, J.; van As, B. A. C; Verbruggen, M.; Roumen, L.; Vekemans, J. A. J. M.; Pieterse, K.; Hil-bers, P. A. J.; Hulshof, L. A.; Palmans, A. R. A.; Meijer, E. W. Switching from S-to R-selectivity in the Candida antarctica lipase B-catalyzed ring-opening of co-methylated lactones: tuning polymerizations by ring size. J. Am. Chem. Soc. 129, 7393-7398(2007).
29. Kondo, A.; Sugihara, S.; Kuwahara, M.; Toshima, K.; Matsumura, S. Lipase-catalyzed ring-opening polymerization of molecularly pure cyclic oligomers for use in synthesis and chemical recycling of aliphatic polyesters. Macromol. Biosci. 8, 533-539 (2008).
30. Yamamoto, Y; Kaihara, S.; Toshima, K; Matsumura, S. High-molecular-weight polycarbonates synthesized by enzymatic ROP of a cyclic carbonate as a green process. Macromol. Biosci. 9, 968-978(2009).
31. Larpent, C; Chasseray, X. Optically active surfactants -I- the fi rst synthesis and properties of sodium bis [(S) -ethyl-2-hexyl] sulfosuccinates (aerosol OT). Tetrahedron 48, 3903-3914(1992).
32. Moss, R. A.; Sunshine, W. L. Critical micelle concentrations of optically active and racemic 2-octylammonium and 2-octyltrimethylammonium ions. J. Org. Chem. 35, 3581-3583 (1970).
33. Moss, R. A.; Sunshine, W. L. Micellar catalysis of ester hydrolysis. The influence of chirality and head group structure in simple surfactants. J. Org. Chem. 39, 1083-1089(1974).