Recent progress for lipase-catalysed synthesis of sugar fatty acid esters

Journal of Oil Palm Research

Volumn 26, Issue 4, 2014, Pages 355-365

  Ye, Ran ^a   Hayes, Douglas G ^a  

^a UNIVERSITY OF TENNESSEE   (United States)

Author keywords

Biobased surfactant; Ionic liquid; Lipase; Solvent free bioconversions; Sugar esters

Indexed keywords

EID: 84919602299     PISSN: 15112780     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (62)

1. ABDEL-MAGEED, H M; EL-LAITHY, H M; MAHRAN, L G; FAHMY, A S; MADER, K and MOHAMED, S A (2012). Development of novel flexible sugar ester vesicles as carrier systems for the antioxidant enzyme catalase for wound healing applications. Process Biochem., 47:1155-1162.
2. ABDUL-RAHEIM, M A; ABDEL-RAOUF, M E; MAYSOUR, N E; EL-KAFRAWY, A F; MEHANY, A Z and ABDEL-AZIM, A (2013). Some sugar fatty ester ethoxylates as demulsifiers for petroleum sludge. J. Surfactants Deterg., 16: 377-387.
3. ABDULMALEK, E; SAUPI, H S M; TEJO, B A; BASRI, M; SALLEH, A B; ABD RAHMAN, R N Z R and ABDUL RAHMAN, M B (2012). Improved enzymatic galactose oleate ester synthesis in ionic liquids. J. Mol Catal. B Enzym., 76: 37-43.
4. ALISSANDRATOS, A and HALLING, P J (2012). Enzymatic acylation of starch. Bioresour. Technol., 225:41-47.
5. ARNING, J and MATZKE, M (2011). Toxicity of ionic liquids towards mammalian cell lines. Curr. Org. Chem., 25:1905-1917.
6. BALLESTEROS, A; PLOU, F J; ALCALDE, M; FERRER, M; GARCIA-ARELLANO, H; REYES- DUARTE, D and GHAZI, I (2007). Enzymatic synthesis of sugar esters and oligosaccharides from renewable resources. Biocatalysis in the Pharmaceutical and Biotechnology Industries (Patel, R N ed.). Boca Raton, FL: CRC Press, p. 463-488.
7. BHATTACHARYA, S C and PALEPU, R M (2004). Micellization of nonionic surfactants. Tweens - A review. J. Surf. Set. Technol, 20:159-177.
8. BALLESTEROS, A; PLOU, F J; ALCALDE, M; FERRER, M; GARCIA-ARELLANO, H; REYES- DUARTE, D and GHAZI, I (2007). Enzymatic synthesis of sugar esters and oligosaccharides from renewable resources. Biocatalysis in the Pharmaceutical and Biotechnology Industries (Patel, R N ed.). Boca Raton, FL: CRC Press, p. 463-488.
9. BHATTACHARYA, S c and PALEPU, R M (2004). Micellization of nonionic surfactants. Tweens - A review. J. Surf. Sci. TcchnoL, 20:159-177.
10. CAO, L; BORNSCHEUER, U T and SCHMID, R D (1999). Lipase-catalyzed solid-phase synthesis of sugar esters. Influence of immobilization on productivity and stability of the enzyme. J. Mol. Catal. B Enz., 6: 279-285.
11. CAO, L; FISCHER, A; BORNSCHEUER, U T and SCHMID, R D (1997). Lipase-catalyzed solid phasesynthesis ot sugar tatty acid esters. Bwcatahjsis Bio- Tmnsform., 14: 269-283.
12. CHANG, S W and SHAW, J F (2009). Biocatalysis for the production of carbohydrate esters. New Biotech- nol., 26:109-116.
13. CHANSANROJ, K and BETZ, G (2010). Sucrose esters with various hydrophilic-lipophilic properties: novel controlled release agents for oral drug delivery matrix tablets prepared by direct compaction. Acta Biomater., 6: 3101-3109.
14. CHORTYK, O T; POMONIS, J G and JOHNSON, A W (1996). Syntheses and characterizations of insec- Ticidal sucrose esters. J. Agric. Food Client., 44: 1551- 1557.
15. CROITORU, R; VAN DEN BROEK, LAM; FRISSEN, A E; DAVIDESCU, C M; PETER, F and BOERIU, C G (2011). Lipase-catalyzed synthesis of aromatic esters of sugar alcohols. World Acad. Sci. Eng. Technol., 52: 484-489.
16. CSOKA, G; MARTON, S; ZELKO, R; OTOMO, N and ANTAL, I (2007). Application of sucrose fatty acid esters in transdermal therapeutic systems. Eur. J. Pharm. Biovharm., 65: 233-237.
17. DURAND, E; LECOMTE, J and VILLENEUVE, P (2013). Deep eutectic solvents: Synthesis, application, and focus on lipase-catalyzed reactions. Eur. J. Lipid Sci. Tecknol, 115: 379-385.
18. FARONE, W A and SERFASS, R (1996). Sugar ester manufacturing process. WO patent 1996-US8934; 9640699.
19. FERRER M; SOLIVERI, J; PLOU, F J; LOPEZ-COR-TES, N; REYES-DUARTE, D; CHRISTENSEN, M; COPA-PATINO, J L and BALLESTEROS, A (2005). Synthesis of sugar esters in solvent mixtures by li-pases from Thcrmomyccs lamiginosus and Candida antarctica B, and their antimicrobial properties. Enz. Microb. Technol, 36: 391-398.
20. FEUGE, R O; ZERINGUE, H J; JR WEISS T J and BROWN, M (1970). Preparation of sucrose esters by interesterification. J. Arner. Oil Chcm. Soc., 47: 56-60.
21. FISCHER, F; HAPPE, M; EMERY, J; FORNAGE, A and SCHUTZ, R (2013). Enzymatic synthesis of 6-and 6 '-O-linoleyl-alpha-D-maltose: from solvent- free to binary ionic liquid reaction media. J. Mol. Catal. B-Enzym., 90: 98-106.
22. FURUKAWA, S; AKIYOSHI, Y; O'TOOLE, G A; OGIHARA, H and MORINAGA, Y (2010). Sugar fatty acid esters inhibit biofilm formation by food-borne pathogenic bacteria. Int. J. Food Microbiol., 138: 176-180.
23. GANSKE, F and BORNSCHEUER, U T (2005). Optimization of lipase-catalvzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t-BuOH. J. Mol. Catal. B Enzym., 36: 40-12.
24. GUMEL, A M; ANNUAR, M S M; HEIDELBERG, T and CHISTI, Y (2011). Lipase mediated synthesis of sugar fatty acid esters. Process Biochem., 46: 2079- 2090.
25. HA, S H; HEEP, N M; LEE, S H and KOO, Y M (2010). Optimization of lipase-catalyzed glucose ester synthesis in ionic liquids. Bioprocess. Biosyst. Eng., 33: 63-70.
26. HEUSCHKEL, S; GOEBEL, A and NEUBERT REIN- HARD, H H (2008). Microemulsions-modern colloidal carrier for dermal and transdermal drug deliver)'. J Pharm Sci, 97: 603-31.
27. JADHAV, S R; VEMULA, P K; KLTMAR, R; RA- GHAVAN, S R and JOHN, G (2010). Sugar-derived phase-selective molecular gelators as model solidifi- ers for oil spills. Angew. Chcrn., Int. Ed., 49:7695-7698, S7695/1-S7695/15.
28. JIN, Z; LIANG, S; ZHANG, X; HAN, S; REN, C; LIN, Y and ZHENG, S (2013). Synthesis of fructose lau- rate esters catalyzed by a CALB-displaying Pichia pas tor is whole-cell biocatalyst in a non-aqueous system. Biotcchnol. Bioprocess Eng., 18: 365-374.
29. JOHN, G; ZHU, G; LI, J and DORDICK, J S (2006). Enzymatically derived sugar-containing self-assembled organogels with nano-structured morphologies. Angew. Chcm., Int. Ed., 45: 4772-4775.
30. KAEWPRAPAN, K; BAROS, F; MARIE, E; INPRAK- HON, P and DURAND, A (2012a). Macromolecular surfactants synthesized by lipase-catalyzed transes- Terification of dextran with vinyl decanoate. Carbo- hydr. Polym., 88: 313-320.
31. KAEWPRAPAN, K; INPRAKHON, P; MARIE, E and DLIRAND, A (2012b). Enzymatically degrada- ble nanoparticles of dextran esters as potential drug delivery systems. Carboliydr. Polym., 88: 875-881.
32. KURAKAKE, M; ITO, Y and KOMAKI, T (2011). Synthesis of sugar fatty acid esters using a f-xylosidase from Aspergillus awamori for transxylosylation. Biotcchnol. Lett 33: 2453-2456.
33. LEE, S H; DANG, D T; HA, S H; CHANG, W-J and KOO, Y-M (2008a). Lipase-catalyzed synthesis of fatty acid sugar ester using extremely supersaturatedsugar solution in ionic liquids. Biotedmol. Bioeng., 99: 1-8.
34. LEE, S H; HA, S H; HIEP, N M; CHANG, W-J and KOO, Y-M (2008b). Lipase-catalyzed synthesis of glucose fatty acid ester using ionic liquid mixtures. J. Biotedmol, 133: 486-489.
35. LIANG, J; ZENG, W; YAO, P and WEI, Y (2012). Lipase-catalyzed regioselective synthesis of palmi- Tolyglucose ester in ionic liquids. Adv. Biol. Chem., 2: 226-232.
36. LIU, T-X; STANSLY, P A and CHORTYK, O T (1996). Insecticidal activity of natural and synthetic sugar esters against Bemisia argentifolii (Homoptera: Aley- rodidac). J. Econ. Entomol., 89:1233-1239.
37. NAKAMURA, S (1999). Application of sucrose fatty acid esters as food emulsifiers. Spec. Publ. - R. Soc. Chem., 230: 73-87.
38. NELEN, BAP and COOPER J M (2004). Sucrose esters. Emulsifiers in Food Technology (Whitehurst, R J ed.). Oxford, UK: Blackwell. p. 131-161.
39. OKAMOTO, H; SAKAI, T and DANJO, K (2005). Effect of sucrose fatty acid esters on transdermal permeation of lidocaine and ketoprofen. Biol. Pharm. Bull., 28:1689-1694.
40. OTOMO, N (2009). Basic properties of sucrose fatty acid esters and their application. Biobascd Surfactants and Detergents: Synthesis, Properties, and Applications (Haves, D G; Kitamoto, D; Solaiman, D K Y and Ashby, R D eds.). Champaign, IL: AOCS Press, p. 275-298.
41. PHAM, T P T; CHO, C-W and YUN, Y-S (2010). Environmental fate and toxicity of ionic liquids: A review. Water Res., 44: 352-372.
42. POLAT, T and LINHARDT, R J (2001). Syntheses and applications of sucrose-based esters. J. Surfactants Deterg., 4: 415-421.
43. PYO, S-H and HAYES, D G (2009). Synthesis of saccharide fatty acid ester biosurfactants catalyzed by lipase. Biobascd Surfactants and Detergents: Synthesis, Properties, and Applications (Hayes, D G; Kitamoto, D; Solaiman, D K Y and Ashby, R D eds.). Champaign, IL USA: AOCS Press, p. 323-350.
44. SHI, Y G; LI, J R and CHU, Y H (2011). Enzyme- catalyzed regioselective synthesis of sucrose-based esters. J. Chem. Technol. Biotechnol, 86: 1457-1468.
45. SONG, Z-J; LI, S-J; XI, C; LILT, L-M and SONG, Z-Q (2006). Synthesis of insecticidal sucrose esters. For. Stud. China, 8: 26-29.
46. TAI, H P and BRUNNER, G (2009). Sugar fatty acid ester synthesis in high-pressure acetone-CO, system. J. Supercrit. Fluids, 48: 36-40.
47. VAN DEN BROEK, LAM and BOERIU, C G (2013). Enzymatic synthesis of oligo- And polysaccharide fatty acid esters. Carbohydr. Polym., 93: 65-72.
48. XIA, Y; JOHNSON, A W and CHORTYK, O T (1998). Toxicity of synthetic sucrose esters against the tobacco aphid (Homoptera: Aphididac). J. Entomol. Sci., 33: 292-299.
49. XIAO, D; YE, R; DAVIDSON, P M; HAYES, D G; GOLDEN, D A and ZHONG, Q (2011). Sucrose mon- olaurate improves the efficacy of sodium hypochlorite against Escherichia coli 0157:H7 on spinach. Int. J. Food Microbiol., 145: 64-68.
50. YAN, F; XIA, S; WANG, Q and MA, P (2012). Predicting the toxicity of ionic liquids in leukemia rat cell line by the quantitative structure-activity relationship method using topological indexes. Ind. Eng. Chan. Res., 51:13897-13901.
51. YANG, Z and HUANG, Z-L (2012). Enzymatic synthesis of sugar fatty acid esters in ionic liquids. Catal. Sci. TechnoL, 2:1767-1775.
52. YAO, P-J; HUANG, G -J; YAN, W; ZHANG, X; LI, Q and WEI, Y-A (2012). Lipase-catalyzed synthesis and characterization of 6-0-(li-dodecenoic)-glucose ester in ionic liquids. Adv. Chcm. Eng. Sci., 2: 204-211.
53. YE, R and HAYES, D G (2011). Optimization of the solvent-free lipase-catalyzed synthesis of fructose- oleic acid ester through programming of water removal. J. Amcr. Oil Chcm. Soc., 88:1351-1359.
54. YE, R and HAYES, D G (2012a). Lipase-catalyzed synthesis of saccharide-fatty acid esters utilizing solvent-free suspensions: effect of acyl donors and acceptors, and enzyme activity retention. J. Amcr. Oil Chan. Soc., 89: 455-463.
55. YE, R and HAYES, D G (2012b). Solvent-free lipase- catalysed synthesis of saccharide-fatty acid esters: closed-loop bioreactor system with in situ formation of metastable suspensions. Biocatal. Biotransfonn., 30: 209-216.
56. YE, R; PYO, S-H and HAYES, D G (2010). Lipase- catalyzed synthesis of saccharide-fatty acid esters using suspensions of saccharide crystals in solvent- free media. J. Amer. Oil Chan. Soc., 87: 281-293.
57. YOUAN BI-BOTTI, C; HUSSAIN, A and NGUYEN NGA, T (2003). Evaluation of sucrose esters as alternative surfactants in microencapsulation of proteins by the solvent evaporation method. AAPS PharmSci, 5: E22.
58. ZHANG, Q; DE OLIVE ERA VIGIER, K; ROYER, S and JEROME, F (2012). Deep eutectic solvents: syntheses, properties and applications. Chan. Soc. Rev., 41: 7108-7146.
59. ZHAO, H and BAKER, G A (2013). Ionic liquids and deep eutectic solvents for biodiesel synthesis: A review. J. Chan. Technol. Biotechnol., 88: 3-12.
60. ZHAO, H; BAKER, G A; SONG, Z; OLUBAJO, O; CRITTLE, T and PETERS, D (2008). Designing en- zyme-compatible ionic liquids that can dissolve carbohydrates. Green Chem., 10: 696-705.
61. ZHAO, H; JONES, C L and COWINS, J V (2009). Lipase dissolution and stabilization in ether-function- Alized ionic liquids. Green Chem., 11: 1128-1138.
62. ZHAO, H; LIU, J; LV, F; YE R; BEE, X; ZHANG, C and LU, Z (2014). Enzymatic synthesis of lard-based ascorbyl esters in a packed-bed reactor: optimization by response surface methodology and evaluation of antioxidant properties. Lwt-Food Sci Technol., 57: 393-399.