Lipase-Catalyzed Synthesis of Sugar Esters in Honey and Agave Syrup

被引:25
作者
Siebenhaller, Sascha [1 ]
Gentes, Julian [1 ]
Infantes, Alba [1 ]
Muhle-Goll, Claudia [2 ,3 ]
Kirschhoefer, Frank [4 ]
Brenner-Weiss, Gerald [4 ]
Ochsenreither, Katrin [1 ]
Syldatk, Christoph [1 ]
机构
[1] Karlsruhe Inst Technol, Inst Proc Engn Life Sci, Tech Biol, Karlsruhe, Germany
[2] Karlsruhe Inst Technol, Inst Organ Chem, Karlsruhe, Germany
[3] Karlsruhe Inst Technol, Inst Biol Interfaces 4, Karlsruhe, Germany
[4] Karlsruhe Inst Technol, Inst Funct Interfaces, Bioengn & Biosyst, Karlsruhe, Germany
关键词
sugar ester; glycolipid synthesis; honey; agave syrup; lipase; transesterification; deep eutectic solvent; SOLID-PHASE SYNTHESIS; FATTY-ACID ESTERS; ENZYMATIC-SYNTHESIS; CARBOHYDRATE; COMPONENTS; PRODUCTS;
D O I
10.3389/fchem.2018.00024
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Honey and agave syrup are high quality natural products and consist of more than 80% sugars. They are used as sweeteners, and are ingredients of cosmetics or medical ointments. Furthermore, both have low water content, are often liquid at room temperature and resemble some known sugar-based deep eutectic solvents (DES). Since it has been shown that it is possible to synthesize sugar esters in these DESs, in the current work honey or, as vegan alternative, agave syrup are used simultaneously as solvent and substrate for the enzymatic sugar ester production. For this purpose, important characteristics of the herein used honey and agave syrup were determined and compared with other available types. Subsequently, an enzymatic transesterification of four fatty acid vinyl esters was accomplished in ordinary honey and agave syrup. Notwithstanding of the high water content for transesterification reactions of the solvent, the successful sugar ester formation was proved by thin-layer chromatography (TLC) and compared to a sugar ester which was synthesized in a conventional DES. For a clear verification of the sugar esters, mass determinations by ESI-Q-ToF experiments and a NMR analysis were done. These environmentally friendly produced sugar esters have the potential to be used in cosmetics or pharmaceuticals, or to enhance their effectiveness.
引用
收藏
页数:9
相关论文
共 50 条
[31]   Lipase-catalyzed Synthesis of Sugar Ester in Mixed Biphasic System of Ionic Liquids and Supercritical Carbon Dioxide [J].
Chang, Panpan ;
Zhang, Zhixia ;
Tang, Shaokun .
JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 2018, 65 (04) :452-458
[32]   Chemometric analysis of lipase-catalyzed synthesis of xylitol esters in a solvent-free system [J].
Adnani, Atena ;
Basri, Mahiran ;
Chaibakhsh, Naz ;
Ahangar, Hossein Abbastabar ;
Salleh, Abu Bakar ;
Rahman, Raja Noor Zaliha Raja Abdul ;
Rahman, Mohd Basyaruddin Abdul .
CARBOHYDRATE RESEARCH, 2011, 346 (04) :472-479
[33]   Effect of alcohol chain length on the optimum conditions for lipase-catalyzed synthesis of adipate esters [J].
Chaibakhsh, Naz ;
Rahman, Mohd Basyaruddin Abdul ;
Basri, Mahiran ;
Salleh, Abu Bakar ;
Rahman, Raja Noor Zaliha Raja Abdul .
BIOCATALYSIS AND BIOTRANSFORMATION, 2009, 27 (5-6) :303-308
[34]   Lipase-catalyzed synthesis of lesquerolic acid wax and diol esters and their properties [J].
Hayes, DG ;
Kleiman, R .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1996, 73 (11) :1385-1392
[35]   Kinetics of lipase-catalyzed synthesis of soybean fatty acid ethyl esters in pressurized propane [J].
Brusamarelo, Claiton Z. ;
Rosset, Eline ;
de Cesaro, Aline ;
Treichel, Helen ;
de Oliveira, Debora ;
Mazutti, Marcio A. ;
Di Luccio, Marco ;
Oliveira, J. Vladimir .
JOURNAL OF BIOTECHNOLOGY, 2010, 147 (02) :108-115
[36]   Lipase-catalyzed polyester synthesis [J].
Wang, ZL ;
Hiltunen, K ;
Orava, P ;
Seppala, J ;
Linko, YY .
JOURNAL OF MACROMOLECULAR SCIENCE-PURE AND APPLIED CHEMISTRY, 1996, A33 (05) :599-612
[37]   Lipase-catalyzed solid-phase synthesis of sugar esters, IV: Selectivity of lipases towards primary and secondary hydroxyl groups in carbohydrates [J].
Cao, LQ ;
Bornscheuer, UT ;
Schmid, RD .
BIOCATALYSIS AND BIOTRANSFORMATION, 1998, 16 (04) :249-257
[38]   Lipase-catalyzed regioselective acylation of sugar in microreactors [J].
Du, Li-Hua ;
Luo, Xi-Ping .
RSC ADVANCES, 2012, 2 (07) :2663-2665
[39]   Lipase mediated synthesis of sugar fatty acid esters [J].
Gumel, A. M. ;
Annuar, M. S. M. ;
Heidelberg, T. ;
Chisti, Y. .
PROCESS BIOCHEMISTRY, 2011, 46 (11) :2079-2090
[40]   Lipase-catalyzed synthesis of fatty acid sugar ester using extremely supersaturated sugar solution in ionic liquids [J].
Lee, Sang Hyun ;
Dang, Dung Thanh ;
Ha, Sung Ho ;
Chang, Woo-Jin ;
Koo, Yoon-Mo .
BIOTECHNOLOGY AND BIOENGINEERING, 2008, 99 (01) :1-8