Enzymatic aminolysis of lactones in aqueous miniemulsion: Catalysis through a novel pathway

Journal of Molecular Catalysis B: Enzymatic

Volumn 62, Issue 3-4, 2010, Pages 270-276

  Ragupathy, Laks ^a,b   Pluhar, Bettina ^a   Ziener, Ulrich ^a   Keller, Harald ^c   Dyllick Brenzinger, Rainer ^c   Landfester, Katharina ^a,b  

^a MAX PLANCK INSTITUTE FOR POLYMER RESEARCH   (Germany)

^b UNIVERSITY OF ULM   (Germany)

^c BASF SE   (Germany)

Author keywords

Amidation; Lipase; Miniemulsion

Indexed keywords

AMIDATION; AMIDE COMPOUNDS; AMINOLYSIS; AQUEOUS CONDITION; CARBOXYLIC GROUP; CONCENTRATION OF; ESTER BONDS; KINETIC INVESTIGATIONS; MINIEMULSIONS; OLEYLAMINE; OPTIMIZED CONDITIONS; REACTION PATHWAYS; REACTION TIME;

AMIDES; ESTERS; HYDROLYSIS;

AMINATION;

CARBOXYLIC ACID; HEXADECANOLIDE; LACTONE; OLEYLAMINE; PENTADECANOLIDE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

AMINOLYSIS; ARTICLE; BIOCATALYST; CATALYSIS; CONCENTRATION RESPONSE; DYNAMIC LIGHT SCATTERING; EMULSION; ENZYME KINETICS; HYDROLYSIS; LIGHT SCATTERING; PH; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION TIME; TEMPERATURE;

EID: 77949918285     PISSN: 13811177     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.molcatb.2009.11.006     Document Type: Article

References (33)

1. Montalbetti C.A.G.N., Falque V. Tetrahedron Lett. 2005, 61:10827-10852.
2. Robins M.J., Sarker S., Xie M., Zhang W., Peterson M.A. Tetrahedron Lett. 1996, 37:3921-3924.
3. Liu W., Xu D.D., Repic O., Blacklock T.J. Tetrahedron Lett. 2001, 42:2439-2441.
4. Musser J.H., VonVoightlander P.F., Szmuszkovicz J. Heterocycles 1986, 24:155-159.
5. Blay G., Cardona L., Garcia B., Garcia C.L., Pedro J.R. Tetrahedron Lett. 1994, 35:931-934.
6. Beerli R., Rebek J. Tetrahedron Lett. 1995, 36:1813-1816.
7. Levin J.I., Turos E., Weinreb S.M. Synth. Commun. 1982, 12:989-993.
8. Bringmann G., Breuning M., Tasler S., Endress H., Ewers C.L.J., Göbel L., Peters K., Peters E.-M. Chem. Eur. J. 1999, 5:3029-3038.
9. Shimizu T., Osako K., Nakata T. Tetrahedron Lett. 1997, 38:2685-2688.
10. Lalli C., Trabocchi A., Menchi G., Guarna A. Synth. Lett. 2007, 2:189-192.
11. Koeller K.M., Wong C.-H. Nature 2001, 409:232-240.
12. Schmid R.D., Verger R. Angew. Chem. Int. Ed. 1998, 37:1608-1633.
13. Klibanov A.M. Acc. Chem. Res. 1990, 23:114-120.
14. Santaniello E., Ferraboschi P., Grisenti P. Enzyme Microb. Technol. 1993, 15:367-382.
15. Santaniello E., Ferraboschi P., Grisenti P., Manzocchi A. Chem. Rev. 1992, 92:1071-1140.
16. Roberts S.M. J. Chem. Soc. Perkin Trans. 1998, 1:157-169.
17. Kobayashi S. Macromol. Rapid Commun. 2009, 30:237-266.
18. Gotor V. Bioorg. Med. Chem. 1999, 7:2189-2197.
19. Gotor-Fernandez V., Gotor V. Curr. Org. Chem. 2006, 10:1125-1143.
20. van Rantwijk F., Sheldon R.A. Tetrahedron Lett. 2004, 60:501-519.
21. Vicente G.-F., Eduardo B., Vicente G. Adv. Synth. Catal. 2006, 348:797-812.
22. Zaks A., Klibanov M. Proc. Natl. Acad. Sci. U.S.A. 1985, 82:3192-3196.
23. Prasad A.K., Husain M., Singh B.K., Gupta R.K., Manchanda V.K., Olsen C.E., Parmar V.S. Tetrahedron Lett. 2005, 46:4511-4514.
24. Levinson W.E., Kuo T.M., Kurtzman C.P. Enzyme Microb. Technol. 2005, 37:126-130.
25. Wouter F.S., Georgina S., David G., Adrie J.J.S., Alain M. Biotechnol. Bioeng. 2003, 82:664-669.
26. Taden A., Antonietti M., Landfester K. Macromol. Rapid Commun. 2003, 24:512-516.
27. Gröger H., May O., Hüsken H., Georgeon S., Drauz K., Landfester K. Angew. Chem. Int. Ed. 2006, 45:1645-1648.
28. Aschenbrenner E.M., Weiss C.K., Landfester K. Chem. Eur. J. 2009, 15:2434-2444.
29. Landfester K. Annu. Rev. Mater. Res. 2006, 36:231-279.
30. Macris J.B., Stamatis H., Kolisis F.N. Appl. Microbiol. Biotechnol. 1996, 46:521-523.
31. Magne F., Mod R., Skau E. Ind. Eng. Chem. 1958, 50:617-618.
32. Jacopin C., Egron M.-J., Scherman D., Herscovici J. Bioorg. Med. Chem. 2002, 12:1447-1450.
33. Kobayashi S., Uyama H., Kimura S. Chem. Rev. 2001, 101:3793-3818.