Enzymatic synthesis of oligo- and polysaccharide fatty acid esters

Carbohydrate Polymers

Volumn 93, Issue 1, 2013, Pages 65-72

  Van Den Broek, Lambertus A M ^a   Boeriu, Carmen G ^a  

^a WAGENINGEN UNIVERSITY   (Netherlands)

Author keywords

Ionic liquids; Lipase; Organic solvents; Protease; Supercritical carbon dioxide

Indexed keywords

ALTERNATIVE ROUTES; AMPHIPHILICS; CHEMICAL METHOD; ENZYMATIC REACTION; ENZYMATIC SYNTHESIS; FATTY ACID ESTERS; FATTY ESTERS; FILM-FORMING PROPERTIES; POLYMERIC SURFACTANT; POLYSACCHARIDE FATTY ACID ESTERS; PROTEASE; STATE OF THE ART; SUPERCRITICAL CARBON DIOXIDES; TOXIC SOLVENTS; WATER SOLUBILITIES;

CARBON DIOXIDE; EMULSIFICATION; ESTERS; IONIC LIQUIDS; LIPASES; ORGANIC SOLVENTS; POLYMERIC FILMS; POLYSACCHARIDES; SUPERCRITICAL FLUID EXTRACTION;

ESTERIFICATION;

BACTERIAL PROTEIN; ESTER; ESTERASE; FATTY ACID; PEPTIDE HYDROLASE; POLYSACCHARIDE; SURFACTANT; TRIACYLGLYCEROL LIPASE;

BACILLUS; BIOCATALYSIS; CHEMISTRY; CONFERENCE PAPER; ENZYME ACTIVATION; ENZYMOLOGY; ESTERIFICATION; SOLUBILITY; SYNTHESIS;

BACILLUS; BACTERIAL PROTEINS; BIOCATALYSIS; ENZYME ACTIVATION; ESTERASES; ESTERIFICATION; ESTERS; FATTY ACIDS; LIPASE; PEPTIDE HYDROLASES; POLYSACCHARIDES; SOLUBILITY; SURFACE-ACTIVE AGENTS;

EID: 84874650303     PISSN: 01448617     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carbpol.2012.05.051     Document Type: Conference Paper

References (54)

1. D.K. Allen, and B.Y. Tao Carbohydrate-alkyl ester derivatives as biosurfactants Journal of Surfactants and Detergents 2 3 1999 383 390
2. M. Arroyo, J.M. Sanchez-Montero, and J.V. Sinisterra Thermal stabilization of immobilized lipase B from Candida antarctica on different supports: Effect of water activity on enzymatic activity in organic media Enzyme and Microbial Technology 24 1-2 1999 3 12
3. 2 in green chemical synthesis and processing Journal of Supercritical Fluids 28 2-3 2004 121 191
4. F. Bordusa Proteases in organic synthesis Chemical Reviews 102 12 2002 4817 4867
5. F.F. Bruno, J.A. Akkara, M. Ayyagari, D.L. Kaplan, R. Gross, and G. Swift Enzymatic modification of insoluble amylose in organic solvents Macromolecules 28 26 1995 8881 8883
6. F.F. Bruno, J.S. Dordick, D.L. Kaplan, and J.A. Akkara Regioselective enzymatic transesterification of polysaccharides in organic solvents R.A. Gross, D.L. Kaplan, G. Swift, Enzymes in polymer synthesis 1998 Amer Chemical Soc Washington 167 174
7. L. Cao Immobilized enzymes M. Moo-Young, Bioreactions and bioreactor operation 2011 Elsevier 461 476
8. G. Carrea, and S. Riva Properties and synthetic applications of enzymes in organic solvents Angewandte Chemie-International Edition 39 13 2000 2226 2254
9. S. Chakraborty, B. Sahoo, I. Teraoka, L.M. Miller, and R.A. Gross Enzyme-catalyzed regioselective modification of starch nanoparticles Macromolecules 38 1 2005 61 68
10. S.W. Chang, and J.F. Shaw Biocatalysis for the production of carbohydrate esters New Biotechnology 26 3-4 2009 109 116
11. Z.G. Chen, M.H. Zong, and G.J. Li Lipase-catalyzed acylation of konjac glucomannan in organic media Process Biochemistry 41 7 2006 1514 1520
12. L. Choisnard, A. Geze, C. Vanhaverbeke, J.B.G. Yameogo, J.L. Putaux, and B. Brasme Physicochemical characterization of alpha-, beta-, and gamma-cyclodextrins bioesterified with decanoate chains used as building blocks of colloidal nanoparticles Biomacromolecules 12 8 2011 3031 3038
13. W. Cui, W.T. Winter, S.W. Tanenbaum, and J.P. Nakas Purification and characterization of an intracellular carboxylesterase from Arthrobacter viscosus NRRL B-1973 Enzyme and Microbial Technology 24 3-4 1999 200 208
14. B.G. Davis, and V. Borer Biocatalysis and enzymes in organic synthesis Natural Product Reports 18 6 2001 618 640
15. I.B. deCarvalho, T.C. deSampaio, and S. Barreiros Solvent effects on the catalytic activity of subtilisin suspended in compressed gases Biotechnology and Bioengineering 49 4 1996 399 404
16. A. Favrelle, V. Bonnet, C. Avondo, F. Aubry, F. Djedaini-Pilard, and C. Sarazin Lipase-catalyzed synthesis and characterization of novel lipidyl-cyclodextrins in solvent free medium Journal of Molecular Catalysis B: Enzymatic 66 1-2 2010 224 227
17. A. Favrelle, V. Bonnet, C. Sarazin, and F. Djedaini-Pilard Novel chemo-enzymatic access to amphiphilic cyclodextrins Journal of Inclusion Phenomena and Macrocyclic Chemistry 57 1-4 2007 15 20
18. A. Fernandez-Mayoralas Synthesis and modification of carbohydrates using glycosidases and lipases Glycoscience: Synthesis of Oligosaccharides and Glycoconjugates 186 1997 1 20
19. L. Ferreira, M.H. Gil, A.M.S. Cabrita, and J.S. Dordick Biocatalytic synthesis of highly ordered degradable dextran-based hydrogels Biomaterials 26 23 2005 4707 4716
20. L. Ferreira, M.H. Gil, R. Carvalho, C. Geraldes, D.Y. Kim, and J.S. Dordick Biocatalytic polytransesterification of inulin with divinyladipate Chemistry of Materials 14 10 2002 4009 4011
21. M. Ferrer, F. Comelles, F.J. Plou, M.A. Cruces, G. Fuentes, and J.L. Parra Comparative surface activities of di- and trisaccharide fatty acid esters Langmuir 18 3 2002 667 673
22. M. Ferrer, M.A. Cruces, F.J. Plou, M. Bernabe, and A. Ballesteros A simple procedure for the regioselective synthesis of fatty acid esters of maltose, leucrose, maltotriose and n-dodecyl maltosides Tetrahedron 56 24 2000 4053 4061
23. M. Ferrer, G. Perez, F.J. Plou, J.V. Castell, and A. Ballesteros Antitumour activity of fatty acid maltotriose esters obtained by enzymatic synthesis Biotechnology and Applied Biochemistry 42 2005 35 39
24. J. Ge, D.A. Lu, J. Wang, and Z. Liu Lipase nanogel catalyzed transesterification in anhydrous dimethyl sulfoxide Biomacromolecules 10 6 2009 1612 1618
25. S. Gremos, D. Zarafeta, D. Kekos, and F. Kolisis Direct enzymatic acylation of cellulose pretreated in BMIMCl ionic liquid Bioresource Technology 102 2 2011 1378 1382
26. A.M. Gumel, M.S.M. Annuar, T. Heidelberg, and Y. Chisti Lipase mediated synthesis of sugar fatty acid esters Process Biochemistry 46 11 2011 2079 2090
27. M.T. Gustavsson, P.V. Persson, T. Iversen, M. Martinelle, K. Hult, and T.T. Teeri Modification of cellulose fiber surfaces by use of a lipase and a xyloglucan endotransglycosylase Biomacromolecules 6 1 2005 196 203
28. P.J. Halling Thermodynamic predictions for biocatalysis in nonconventional media - Theory, tests, and recommendations for experimental-desing and analysis Enzyme and Microbial Technology 16 3 1994 178 206
29. K. Kaewprapan, P. Tuchinda, E. Marie, A. Durand, and P. Inprakhon PH-imprinted lipase catalyzed synthesis of dextran fatty acid ester Journal of Molecular Catalysis B: Enzymatic 47 3-4 2007 135 142
30. K. Kaewprapan, J. Wongkongkatep, W. Panbangred, P. Phinyocheep, E. Marie, and A. Durand Lipase-catalyzed synthesis of hydrophobically modified dextrans: Activity and regioselectivity of lipase from Candida rugosa Journal of Bioscience and Bioengineering 112 2 2011 124 129
31. J.F. Kennedy, H. Kumar, P.S. Panesar, S.S. Marwaha, R. Goyal, and A. Parmar Enzyme-catalyzed regioselective synthesis of sugar esters and related compounds Journal of Chemical Technology and Biotechnology 81 6 2006 866 876
32. C. Laane, S. Boeren, K. Vos, and C. Veeger Rules for optimizationof biocatalysis in organic solvents Biotechnology and Bioengineering 30 1 1987 81 87
33. P.M. Nielsen, J. Brask, and L. Fjerbaek Enzymatic biodiesel production: Technical and economical considerations European Journal of Lipid Science and Technology 110 8 2008 692 700
34. N.R. Pedersen, J.B. Kristensen, G. Bauw, B.J. Ravoo, R. Darcy, and K.L. Larsen Thermolysin catalyses the synthesis of cyclodextrin esters in DMSO Tetrahedron: Asymmetry 16 3 2005 615 622
35. I. Perez-Victoria, and J.C. Morales Complementary regioselective esterification of non-reducing oligosaccharides catalyzed by different hydrolases Tetrahedron 62 5 2006 878 886
36. I. Perez-Victoria, and J.C. Morales Regioselectivity in acylation of oligosaccharides catalyzed by the metalloprotease thermolysin Tetrahedron 62 10 2006 2361 2369
37. I. Perez-Victoria, and J.C. Morales One- and two-step enzymatic synthesis of polymerizable vinyladipoyl mono- and diesters of non-reducing trisaccharides Journal of Molecular Catalysis B: Enzymatic 48 1-2 2007 8 15
38. F.J. Plou, M.A. Cruces, M. Ferrer, G. Fuentes, E. Pastor, and M. Bernabe Enzymatic acylation of di- and trisaccharides with fatty acids: Choosing the appropriate enzyme, support and solvent Journal of Biotechnology 96 1 2002 55 66
39. F.J. Plou, M.A. Cruces, E. Pastor, M. Ferrer, M. Bernabe, and A. Ballesteros Acylation of sucrose with vinyl esters using immobilized hydrolases: Demonstration that chemical catalysis may interfere with enzymatic catalysis Biotechnology Letters 21 7 1999 635 639
40. T. Polat, and R.J. Linhardt Syntheses and applications of sucrose-based esters Journal of Surfactants and Detergents 4 4 2001 415 421
41. A. Rajan, V.S. Prasad, and T.E. Abraham Enzymatic esterification of starch using recovered coconut oil International Journal of Biological Macromolecules 39 4-5 2006 265 272
42. S. Riva, J. Chopineau, A.P.G. Kieboom, and A.M. Klibanov Protease-catalyzed regioselective esterification of sugars and related compounds in anydrous dimethylformamide Journal of the American Chemical Society 110 2 1988 584 589
43. S. Riva, M. Nonini, G. Ottolina, and B. Danieli Subtilisin-catalyzed esterification of di- and oligosaccharides containing a D-fructose moiety Carbohydrate Research 314 3-4 1998 259 266
44. 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 2 2008 359 361
45. V. Sereti, H. Stamatis, E. Koukios, and F.N. Kolisis Enzymatic acylation of cellulose acetate in organic media Journal of Biotechnology 66 2-3 1998 219 223
46. V. Sereti, H. Stamatis, C. Pappas, M. Polissiou, and F.N. Kolisis Enzymatic acylation of hydroxypropyl cellulose in organic media and determination of ester formation by diffuse reflectance infrared Fourier transform (DRIFT) spectroscopy Biotechnology and Bioengineering 72 4 2001 495 500
47. R.A. Sheldon Green solvents for sustainable organic synthesis: State of the art Green Chemistry 7 5 2005 267 278
48. R. ter Haar, H.A. Schols, L.A.M. van den Broek, D. Saglam, 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 2 2010 183 189
49. H.K. Weber, H. Stecher, and K. Faber Sensitivity of microbial lipases to acetaldehyde formed by acyl-transfer reactions from vinyl esters Biotechnology Letters 17 8 1995 803 808
50. J.B. Xie, and Y.L. Hsieh Enzyme-catalyzed transesterification of vinyl esters on cellulose solids Journal of Polymer Science Part A: Polymer Chemistry 39 11 2001 1931 1939
51. A.R.M. Yahya, W.A. Anderson, and M. Moo-Young Ester synthesis in lipase-catalyzed reactions Enzyme and Microbial Technology 23 7-8 1998 438 450
52. K. Yang, and Y.J. Wang Lipase-catalyzed cellulose acetylation in aqueous and organic media Biotechnology Progress 19 6 2003 1664 1671
53. K. Yang, Y.J. Wang, and M.I. Kuo Effects of substrate pretreatment and water activity on lipase-catalyzed cellulose acetylation in organic media Biotechnology Progress 20 4 2004 1053 1061
54. H. Zhao, G.A. Baker, Z.Y. Song, O. Olubajo, T. Crittle, and D. Peters Designing enzyme-compatible ionic liquids that can dissolve carbohydrates Green Chemistry 10 6 2008 696 705