Abstract
Myristoyl maltose ester was synthesized by lipase-catalyzed reaction of maltose and myristic acid. Influence of different reaction parameters, such as molecular sieve concentration, molar ratio of acid/sugar, enzyme concentration, reaction time, and reaction temperature, was studied. Under the optimum conditions of 20 g/L molecular sieve, 14% (w/w) lipase from Novozym 435, and acid/sugar molar ratio of 5:1 at 60 °C for 60 h, the highest conversion (90%) was achieved. The as-prepared maltose ester was confirmed by Fourier-transform infrared spectra (FTIR), liquid chromatograph–mass spectrum (LC–MS), and scanning electron microscopy (SEM).
Similar content being viewed by others
References
Ganske F, Bornscheur TU (2005) Optimization of lipase-catalyzed glucose fatty acid ester synthesis in a two-phase system containing ionic liquids and t-BuOH. J Mol Catal B: Enzym 36:40–42
Victoria PI, Zafra A, Morales CJ (2007) Determination of regioisomeric distribution in carbohydrate fatty acid monoesters by LC-ESI-MS. Carbohydr Res 342:236–242
Antczak T, Patura J, Antczak SM, Hiler D, Bielecki S (2004) Sugar ester synthesis by a mycelium-bound Mucor circinelloides lipase in a micro-reactor equipped with water activity sensor. J Mol Catal B: Enzym 29:155–161
Blecker C, Danthine S, Pétré M, Lognay G, Moreau B, Vander EL, Paquot M, Deroanne C (2008) Enzymatically prepared n-alkyl esters of glucuronic acid: The effect of freeze-drying conditions and hydrophobic chain length on thermal behavior. J Colloid Interface Sci 321:154–158
Francisco PJ, Angeles CM, Ferrer M, Fuentes G, Pastor E, Bernabe′ M, Christensen M, Comelles F, Parra JL, Ballesteros A (2002) Enzymatic acylation of di- and trisaccharides with fatty acids: choosing the appropriate enzyme, support and solvent. J Biotechnol 96:55–66
Manuel F, Cruces AM, Plou JF, Bernabea M, Ballesteros A (2000) A simple procedure for the regioselective synthesis of fatty acid esters of maltose, leucrose, maltoriose and n-dodecyl malosides. Tetrahedron 56:4053–4061
Polat T, Linhardt R (2001) Synthesis and applications of sucrose-based esters. J Surf Deterg 4:415–421
Habulin M, Šabeder S, Knez Ž (2008) Enzymatic synthesis of sugar fatty acid esters in organic solvent and in supercritical carbon dioxide and their antimicrobial activity. J Supercrit Fluids 45:338–345
Chortyk OT (1996) Synthesis and characterization of insecticidal sucrose esters. J Agric Food Chem 44:1551–1557
Sabeder S, Habulin M, Knez Z (2006) Lipase-catalyzed synthesis of fatty acid fructose esters. J Food Eng 77:880–886
Lee HS, Ha HS, Hiep MN, Chang JW, Koo MY (2008) Lipase-catalyzed synthesis of glucose fatty acid esters using ionic liquids mixtures. J Biochem 133:486–489
Watanabe T, Katayama S, Matsubara M, Honda Y, Kuwahara M (2000) Antibacterial mutants in the presence of sucrose. Curr Microbiol 41:210–213
Adachi S, Kobayashi T (2005) Synthesis of esters by immobilized-lipase-catyalyzed condensation reaction of sugar and fatty acids in water-miscibe organic solvent. Biosci Bioeng 99:87–94
Kaewprapan K, Tuchinda P, Marie E, Durand A, Inprakhon P (2007) Ph-imprinted lipase catalyzed synthesis of dextran fatty acid ester. J Mol Catal B: Enzym 47:135–142
Piao J, Takase K, Adachi S (2007) Enzymatic synthesis of myristoyl disaccharides and their surface activity. J Sci Food Agric 87:1743–1747
Sakaki K, Aoyama A, Nakane T, Ikegami T, Negishi H, Watanabe K, Yanagishita H (2006) Enzymatic synthesis of sugar esters in organic solvent coupled with pervaporation. Desalination 193:260–266
Borges RM, Santos DAJ, Vieira M, Balaban R (2009) Polymerization of a water soluble glucose vinyl ester monomer with tensoactive properties synthesized by enzymatic catalyst. Mater Sci Eng C 29:519–523
Kuroiwa T, Kimura K, Ichikawa S, Nakajima M, Sato S, Mukataka S (2007) Lipase-catalysed synthesis of fatty acid modified chitobiose in a low-water organic solvent effect of water distribution in a multiphase reaction system. Inst Chem Eng 85:98–103
Liu Q.-Y, Jia C.-S, Jiang P.-P, Zhang X.-M, Feng B, Xu S.-Y (2008) Selective synthesis of monolauroyl maltose in acetone by immobilized lipase. Fine Chem (In Chinese) 25:139–146
Tarahomjoo S, Alemzadeh I (2003) Surfactant production by an enzymatic method. Enzym Microb Technol 33:33–37
Cauglia F, Canepa P (2008) The enzymatic synthesis of glucosylmyristate as a reaction model for general considerations on ‘sugar esters’ production. Biores Technol 99:4065–4072
Ferrer M, Soliveri J, Plou JF, Cortes LN, Duarte RD, Christensen M, Patino CJ, Ballesteros A (2005) Synthesis of sugar esters in solvent mixtures by lipase from Thermomyces lanuginosus and Candida Antarctica B, and their antimicrobial properties. Enzym Microb Technol 36:391–398
Arcos JA, Hill CG, Otero C (2001) Kinetics of the lipase-catalyzed of glucose esters in acetone. Biotechnol Bioeng 73:104–110
Acknowledgments
This work is financially supported by National 863 Project grant (No. 2007AA100401).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Sun, P., Chen, Y., Wang, H. et al. Lipase-catalyzed synthesis and characterization of myristoyl maltose ester. Eur Food Res Technol 233, 253–258 (2011). https://doi.org/10.1007/s00217-011-1490-0
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00217-011-1490-0