Novel surface-active oligofructose fatty acid mono-esters by enzymatic esterification

Food Chemistry

Volumn 138, Issue 2-3, 2013, Pages 1884-1891

  Van Kempen, Silvia E H J ^a   Boeriu, Carmen G ^a   Schols, Henk A ^a   De Waard, Pieter ^a   Van Der Linden, Erik ^a   Sagis, Leonard M C ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Enzymatic esterification; Fatty acid chain length; Food grade surfactant; Lipase; Oligofructose

Indexed keywords

AMPHIPHILICITY; CANDIDA ANTARCTICA LIPASE; DILATATIONAL MODULUS; ENZYMATIC ESTERIFICATION; FATTY ACID CHAINS; FATTY ACID ESTERS; FOOD GRADE; MALDI-TOF-MS ANALYSIS; MONOESTERS; OLIGO-FRUCTOSE; REVERSE PHASE; SOLID-PHASE EXTRACTION;

CHAIN LENGTH; ESTERS; LIPASES; SURFACE ACTIVE AGENTS; SURFACE TENSION;

ESTERIFICATION;

AMPHOPHILE; DIMETHYL SULFOXIDE; FRUCTOSE OLIGOSACCHARIDE; LAURIC ACID; LIPASE B; OCTANOIC ACID; PALMITIC ACID; STEARIC ACID;

AMINO ACID SYNTHESIS; ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; CATALYST; CHEMICAL REACTION; ENZYME ACTIVITY; ENZYME SPECIFICITY; ESTERIFICATION; HYDROPHOBICITY; LIPOPHILICITY; MATRIX ASSISTED LASER DESORPTION IONIZATION TIME OF FLIGHT MASS SPECTROMETRY; NONHUMAN; REACTION TIME; SOLID PHASE EXTRACTION; SOLUBILITY; SURFACE TENSION; TRANSESTERIFICATION;

CANDIDA; ESTERIFICATION; ESTERS; FATTY ACIDS; FUNGAL PROTEINS; LIPASE; MOLECULAR STRUCTURE; OLIGOSACCHARIDES; SURFACE-ACTIVE AGENTS;

CANDIDA ANTARCTICA;

EID: 84873706796     PISSN: 03088146     EISSN: 18737072     Source Type: Journal    
DOI: 10.1016/j.foodchem.2012.09.133     Document Type: Article

References (33)

1. M.A. Bos, and T. Van Vliet Interfacial rheological properties of adsorbed protein layers and surfactants: A review Advances in Colloid and Interface Science 91 2001 437 471
2. D. Bosscher, J. Van Loo, and A. Franck Inulin and oligofructose as functional ingredients to improve bone mineralization International Dairy Journal 16 2006 1092 1097
3. L. Cao, U.T. Bornscheuer, and R.D. Schmid Lipase-catalyzed solid-phase synthesis of sugar esters. Influence of immobilization on productivity and stability of the enzyme Journal of Molecular Catalysis B: Enzymatic 6 1999 279 285
4. L. Cao, A. Fischer, U.T. Bornscheuer, and R.D. Schmid Lipase-catalyzed solid phase synthesis of sugar fatty acid esters Biocatalysis and Biotransformation 14 1997 269 283
5. B. Chen, J. Hu, E.M. Miller, W. Xie, M. Cai, and R.A. Gross Candida antarctica lipase B chemically immobilized on epoxy-activated micro- and nanobeads: Catalysts for polyester synthesis Biomacromolecules 9 2008 463 471
6. D. Coulon, M. Girardin, and M. Ghoul Enzymic synthesis of fructose monooleate in a reduced pressure pilot scale reactor using various acyl donors Process Biochemistry 34 1999 913 918
7. D. Coulon, A. Ismail, M. Girardin, and M. Ghoul Enzymatic synthesis of alkylglycoside fatty acid esters catalyzed by an immobilized lipase Journal of Molecular Catalysis B: Enzymatic 5 1998 45 48
8. D. Coulon, A. Ismail, M. Girardin, B. Rovel, and M. Ghoul Effect of different biochemical parameters on the enzymatic synthesis of fructose oleate Journal of Biotechnology 51 1996 115 121
9. J.F. Cramer, M.S. Dueholm, S.B. Nielsen, D.S. Pedersen, R. Wimmer, and L.H. Pedersen Controlling the degree of esterification in lipase catalysed synthesis of xylitol fatty acid esters Enzyme and Microbial Technology 41 2007 346 352
10. P. Degn, K.L. Larsen, J.Ø. Duus, B.O. Petersen, and W. Zimmermann Two-step enzymatic synthesis of maltooligosaccharide esters Carbohydrate Research 329 2000 57 63
11. P. Degn, L.H. Pedersen, J.Ø. Duus, and W. Zimmermann Lipase-catalysed synthesis of glucose fatty acid esters in tert-butanol Biotechnology Letters 21 1999 275 280
12. L. Ferreira, M.H. Gil, R. Carvalho, C.F.G.C. Geraldes, D.Y. Kim, and J.S. Dordick Biocatalytic polytransesterification of inulin with divinyladipate Chemistry of Materials 14 2002 4009 4011
13. D.I. Habeych, P.B. Juhl, J. Pleiss, D. Vanegas, G. Eggink, and C.G. Boeriu Biocatalytic synthesis of polyesters from sugar-based building blocks using immobilized Candida antarctica lipase B Journal of Molecular Catalysis B: Enzymatic 71 2011 1 9
14. M. Habulin, S. Šabeder, and Ž. Knez Enzymatic synthesis of sugar fatty acid esters in organic solvent and in supercritical carbon dioxide and their antimicrobial activity The Journal of Supercritical Fluids 45 2008 338 345
15. A. Hoppe, and R.R. Theimer Titrimetric test for lipase activity using stabilized triolein emulsions Phytochemistry 42 1996 973 978
16. I. Kralova, and J. Sjöblom Surfactants used in food industry: A review Journal of Dispersion Science and Technology 30 2009 1363 1383
17. X.F. Li, M.H. Zong, H. Wu, and W.Y. Lou Markedly improving Novozym 435-mediated regioselective acylation of 1-β-d-arabinofuranosylcytosine by using co-solvent mixtures as the reaction media Journal of Biotechnology 124 2006 552 560
18. N.R. Pedersen, R. Wimmer, J. Emmersen, P. Degn, and L.H. Pedersen Effect of fatty acid chain length on initial reaction rates and regioselectivity of lipase-catalysed esterification of disaccharides Carbohydrate research 337 2002 1179 1184
19. I. Pérez-Victoria, and J.C. Morales Complementary regioselective esterification of non-reducing oligosaccharides catalyzed by different hydrolases Tetrahedron 62 2006 878 886
20. J. Piao, K. Takase, and S. Adachi Enzymatic synthesis of myristoyl disaccharides and their surface activity Journal of the Science of Food and Agriculture 87 2007 1743 1747
21. J. Pleiss, M. Fischer, and R.D. Schmid Anatomy of lipase binding sites: The scissile fatty acid binding site Chemistry and Physics of Lipids 93 1998 67 80
22. S. Riva, M. Nonini, G. Ottolina, and B. Danieli Subtilisin-catalyzed esterification of di- and oligosaccharides containing a d-fructose moiety Carbohydrate Research 314 1998 259 266
23. M.B. Roberfroid Inulin-type fructans: Functional food ingredients Journal of Nutrition 137 2007 2493S 2502S
24. S. Šabeder, M. Habulin, and Ž. Knez Lipase-catalyzed synthesis of fatty acid fructose esters Journal of Food Engineering 77 2006 880 886
25. L.M.C. Sagis, C.G. Boeriu, G.E. Frissen, H.A. Schols, and P.A. Wierenga Highly stable foams from block oligomers synthesized by enzymatic reactions Langmuir 24 2008 359 361
26. D.B. Sarney, and E.N. Vulfson Application of enzymes to the synthesis of surfactants Trends in Biotechnology 13 1995 164 172
27. S. Soultani, J.-M. Engasser, and M. Ghoul Effect of acyl donor chain length and sugar/acyl donor molar ratio on enzymatic synthesis of fatty acid fructose esters Journal of Molecular Catalysis B: Enzymatic 11 2001 725 731
28. S. Tarahomjoo, and I. Alemzadeh Surfactant production by an enzymatic method Enzyme and Microbial Technology 33 2003 33 37
29. R. Ter Haar, H.A. Schols, L.A.M. Van den Broek, D. Saǧlam, A.E. Frissen, and C.G. Boeriu Molecular sieves provoke multiple substitutions in the enzymatic synthesis of fructose oligosaccharide-lauryl esters Journal of Molecular Catalysis B: Enzymatic 62 2010 183 189
30. L.A.M. van den Broek, and C.G. Boeriu Enzymatic synthesis of oligo- and polysaccharide fatty acid esters Carbohydrate Polymers 2012 10.1016/j.carbpol. 2012.05.051
31. A. Widjaja, T.H. Yeh, and Y.H. Ju Enzymatic synthesis of caffeic acid phenethy1 ester Journal of the Chinese Institute of Chemical Engineers 39 2008 413 418
32. M. Woudenberg-Van Oosterom, F. Van Rantwijk, and R.A. Sheldon Regioselective acylation of disaccharides in tert-butyl alcohol catalyzed by Candida antarctica lipase Biotechnology and Bioengineering 49 1996 328 333
33. A. Zaks, and A.M. Klibanov Enzymatic catalysis in nonaqueous solvents Journal of Biological Chemistry 263 1988 3194 3201