Biocatalytic acylation of sugar alcohols by 3-(4-hydroxyphenyl)propionic acid

Process Biochemistry

Volumn 47, Issue 12, 2012, Pages 1894-1902

  Croitoru, R ^a   Fitigau F ^a   Van Den Broek, L A M ^b   Frissen, A E ^b   Davidescu, C M ^a   Boeriu, C G ^b,c   Peter, F ^a  

^a POLITEHNICA UNIVERSITY OF TIMISOARA   (Romania)

^b WAGENINGEN UNIVERSITY   (Netherlands)

^c AUREL VLAICU UNIVERSITY OF ARAD   (Romania)

Author keywords

Aromatic ester; Biocatalysis; Candida antarctica; Lipase; Sugar alcohol

Indexed keywords

AROMATIC ESTERS; BIOCATALYSIS; CANDIDA ANTARCTICA; CATALYTIC EFFICIENCIES; COSMETIC FORMULATIONS; DIESTERS; ENZYMATIC SYNTHESIS; MALDI TOF MS; MOLAR RATIO; MONOESTERS; NOVOZYME 435; ORGANIC SOLVENT MEDIUM; PROPIONIC ACIDS; REACTION PARAMETERS; SUGAR ALCOHOLS; TERT BUTANOL; TRIESTERS;

AROMATIC COMPOUNDS; DRUG PRODUCTS; ENZYMES; ESTERIFICATION; ESTERS; ISOMERS; LIPASES; MOLECULAR SIEVES; ORGANIC SOLVENTS; SATURATED FATTY ACIDS; SPECTRUM ANALYSIS; SUGAR SUBSTITUTES;

ALCOHOLS;

CANDIDA ANTARCTICA;

EID: 84870853337     PISSN: 13595113     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.procbio.2012.06.015     Document Type: Article

References (39)

1. E. Anouar, P. Košinová, D. Kozlowski, R. Mokrini, and J.L. Duroux New aspects of the antioxidant properties of phenolic acids: a combined theoretical and experimental approach Phys Chem Chem Phys 11 2009 7659 7668
2. K. Ravichandran, A.R. Ahmed, D. Knorr, and I. Smetanska The effect of different processing methods on phenolic acid content and antioxidant activity of red beet Food Res Int 48 1 2012 16 20
3. K. Sabally, S. Karboune, F.K. Yeboah, and S. Kermasha Lipase-catalyzed esterification of selected phenolic acids with linolenyl alcohols in organic solvent media Appl Biochem Biotechnol 127 1 2005 17 27
4. A. Bernhaus, M. Fritzer-Szekeres, M. Grusch, P. Saiko, G. Krupitza, S. Venkateswarlu, G. Trimurtulu, W. Jaeger, and T. Szekeres Digalloylresveratrol, a new phenolic acid derivative induces apoptosis and cell cycle arrest in human HT-29 colon cancer cells Cancer Lett 274 2 2009 299 304
5. S. Cheenpracha, E-J. Park, W.Y. Yoshida, C. Barit, M. Wali, J.M. Pezzuto, and L.C. Chang Potential anti-inflammatory phenolic glucosides from the medicinal plant Moringa oleifera fruits Bioorg Med Chem 18 17 2010 6598 6602
6. 2, and TNF-α production Bioorg Med Chem Lett 19 15 2009 4389 4393
7. R.T. Otto, H. Scheib, U.T. Bornscheuer, J. Pleiss, C. Syldatk, and R.D. Schmid Substrate specificity of lipase B from Candida antarctica in the synthesis of arylaliphatic glycolipids J Mol Catal B: Enzym 8 4-6 2000 201 211
8. K.R. Määttä-Riihinen, A. Kamal-Eldin, and A. Riitta Törrönen Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (Family Rosaceae) J Agric Food Chem 52 20 2004 6178 6187
9. J.H. Chen, and C.T. Ho Antioxidant activities of caffeic acid and its related hydroxycinnamic acid compounds J Agric Food Chem 45 7 1997 2374 2378
10. A.F. Artamonov, L.F. Burkovskaya, F.S. Nigmatullina, and Dzhiembaev B.Zh Synthesis of monoesters of d-sorbitol and aromatic acids Chem Nat Compd 33 5 1997 571 573
11. G. Csajágics Szatzker, E.R. Tke, L. Ürge, F. Darvas, and L. Poppe Enantiomer selective acylation of racemic alcohols by lipases in continuous-flow bioreactors Tetrahedron: Asymmetry 19 2008 237 246
12. M. Singh, R.S. Singh, and U.C. Banerjee Enantioselective transesterification of racemic phenyl ethanol and its derivatives in organic solvent and ionic liquid using Pseudomonas aeruginosa lipase Process Biochem 45 1 2010 25 29
13. R.D. Schmid, and Verger R. Lipases Interfacial enzymes with attractive applications Angew Chem Int Ed 37 1998 1608 1633
14. U.T. Bornscheuer, and R.J. Kazlauskas Hydrolases in Organic Synthesis - Regio- and Stereoselective Biotransformations 1999 Wiley-VCH Weinheim
15. E.M. Anderson, K.M. Larsson, and O. Kirk One biocatalyst-many applications: the use of Candida antarctica B-lipase in organic synthesis Biocatal Biotransform 16 1998 181 204
16. J.F. Kennedy, H. Kumar, P.S. Panesar, S.S. Marwaha, R. Goyal, A. Parmar, and S. Kaur Enzyme-catalyzed regioselective synthesis of sugar esters and related compounds J Chem Technol Biotechnol 81 2006 866 876
17. L. Cao, A. Fischer, U.T. Bornscheuer, and R.D. Schmid Lipase-catalyzed solid phase synthesis of sugar fatty esters Biocatal Biotransform 14 4 1996 269 283
18. M. Ferrer, J. Soliveri, F.J. Plou, N. López-Cortés, D. Reyes-Duarte, M. Christensen, J.L. Copa-Patino, and A. Ballesteros Synthesis of sugar esters in solvent mixtures by lipases from Thermomyces lanuginosus and Candida antarctica B, and their antimicrobial properties Enzyme Microb Technol 36 2005 391 398
19. R.T. Otto, U.T. Bornscheuer, H. Scheib, J. Pleiss, C. Syldatk, and R.D. Schmid Lipase-catalyzed esterification of unusual substrates: synthesis of glucuronic acid and ascorbic acid (vitamin C) esters Biotechnol Lett 20 11 1998 1091 1094
20. A. Ducret, A. Giroux, M. Trani, and R. Lortie Enzymatic preparation of biosurfactants from sugar alcohols and fatty acids in organic media under reduced pressure Biotechnol Bioeng 48 1995 214 221
21. J. Piao, and S. Adachi Enzymatic preparation of fatty acid esters of sugar alcohols by condensation in acetone using a packed-bed reactor with immobilized Candida antarctica lipase Biocatal Biotransform 22 4 2004 269 274
22. A. Adnani, M. Basri, N. Chaibakhsh, H.A. Ahangar, A.B. Salleh, R.N.Z.R. Abdul Rahman, and M.B. Abdul Rahman Chemometric analysis of lipase-catalyzed synthesis of xylitol esters in a solvent-free system Carbohydr Res 346 4 2011 472 479
23. C. Otero, J.A. Arcos, M.A. Berrendero, and C. Torres Emulsifiers from solid and liquid polyols: different strategies for obtaining optimum conversions and selectivities J Mol Catal B: Enzym 11 2001 883 892
24. G.J.H. Buisman, C.T.W. van Helteren, G.F.H. Kramer, J.W. Veldsink, J.T.P. Derksen, and F.P. Cuperus Enzymatic esterifications of functionalized phenols for the synthesis of lipophilic antioxidants Biotechnol Lett 20 2 1998 131 136
25. M. Zoumpanioti, E. Merianou, T. Karandreas, H. Stamatis, and A. Xenakis Esterification of phenolic acids catalyzed by lipases immobilized in organogels Biotechnol Lett 32 10 2010 1457 1462
26. Z. Yang, Z. Guo, and X. Xu Enzymatic lipophilisation of phenolic acids through esterification with fatty alcohols in organic solvents Food Chem 132 3 2012 1311 1315
27. D.E. Stevenson, R. Wibisono, D.J. Jensen, R.A. Stanley, and J.M. Cooney Direct acylation of glycosides with phenolic acids catalysed by Candida antarctica lipase B (Novozyme 435) Enzyme Microb Technol 39 2006 1236 1241
28. M. Nagata Synthesis, characterization, and hydrolytic degradation of copolyesters of 3-(4-hydroxyphenyl)propionic acid and p-hydroxybenzoic acid, vanilic acid, or syringic acid J Appl Polym Sci 78 14 2000 2474 2481
29. H.R. Kricheldorf, and T. Stukenbrock New polymer syntheses, 92. Biodegradable, thermotropic copolyesters derived from β-(4-hydroxyphenyl) propionic acid Macromol Chem Phys 198 11 1997 3753 4376
30. R. Croitoru, L.A.M. van den Broek, A.E. Frissen, C.M. Davidescu, F. Peter, and C.G. Boeriu Lipase catalyzed synthesis of aromatic esters of sugar alcohols World Acad Sci Eng Technol 76 2011 484 489
31. E. Castillo, F. Pezzotti, A. Navarro, and A. López-Munguía Lipase-catalyzed synthesis of xylitol monoesters: solvent engineering approach J Biotechnol 102 2003 251 259
32. P. Degn, and W. Zimmermann Optimization of carbohydrate fatty acid ester synthesis in organic media by a lipase from Candida antarctica Biotechnol Bioeng 74 6 2001 483 491
33. T. Kobayashi Lipase-catalyzed syntheses of sugar esters in non-aqueous media Biotechnol Lett 33 10 2011 1911 1919
34. J.A. Arcos, M. Bernabe, and C. Otero Quantitative enzymatic production of 1,6-diacyl sorbitol esters Biotechnol Bioeng 60 1998 53 60
35. A. Zaks, and A.M. Klibanov Enzymatic catalysis in non-aqueous solvents J Biol Chem 263 7 1988 3194 3201
36. S. Naik, A. Basu, R. Saikia, B. Madan, P. Paul, R. Chaterjee, J. Brask, and A. Svendsen Lipases for use in industrial biocatalysis: specificity of selected structural groups of lipases J Mol Catal B: Enzym 65 2010 18 23
37. 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 J Mol Catal B: Enzym 6 1999 279 285
38. J. Hu, W. Gao, A. Kulshrestha, and R.A. Gross Lipase-catalyzed condensation-polymerization of alditols Macromolecules 39 2006 6789 6792
39. M. Miljkovič Carbohydrates: Synthesis, Mechanisms and Stereoelectronical Effects 2009 Springer Science + Business Media New York p. 32-3