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
[21]   Lipase-Catalyzed Synthesis of a Sugar Alcohol-Based Nonionic Surfactant [J].
Adnani, Atena ;
Basri, Mahiran ;
Chaibakhsh, Naz ;
Salleh, Abu Bakar ;
Rahman, Mohd Basyaruddin Abdul .
ASIAN JOURNAL OF CHEMISTRY, 2011, 23 (01) :388-392
[22]   Lipase-catalyzed synthesis of kojic acid esters in organic solvents [J].
Liu, KJ ;
Shaw, JF .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1998, 75 (11) :1507-1511
[23]   Lipase-catalyzed synthesis of β-methylglucoside esters containing an α-hydroxy acid [J].
Park, DW ;
Kim, JS ;
Haam, S ;
Kim, HS ;
Kim, WS .
BIOTECHNOLOGY LETTERS, 2001, 23 (23) :1947-1952
[24]   Lipase-catalyzed synthesis of chlorogenate fatty esters in solvent-free medium [J].
Giraldo, Luis J. Lopez ;
Laguerre, Mickael ;
Lecomte, Jerome ;
Figueroa-Espinoza, Maria-Cruz ;
Barouh, Nathalie ;
Barea, Bruno ;
Villeneuve, Pierre .
ENZYME AND MICROBIAL TECHNOLOGY, 2007, 41 (6-7) :721-726
[25]   Lipase-Catalyzed Esterification of Geraniol and Citronellol for the Synthesis of Terpenic Esters [J].
Layane da Silva Corrêa ;
Rosana Oliveira Henriques ;
João Vitor Rios ;
Lindomar Alberto Lerin ;
Débora de Oliveira ;
Agenor Furigo .
Applied Biochemistry and Biotechnology, 2020, 190 :574-583
[26]   LIPASE-CATALYZED PRODUCTION OF WAX ESTERS [J].
TRANI, M ;
ERGAN, F ;
ANDRE, G .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 1991, 68 (01) :20-22
[27]   Lipase-catalyzed synthesis of a sugar ester containing arachidonic acid [J].
Ward, OP ;
Fang, JW ;
Li, ZY .
ENZYME AND MICROBIAL TECHNOLOGY, 1997, 20 (01) :52-56
[28]   Lipase-catalyzed synthesis of glucose-6-O-hexanoate in deep eutectic solvents [J].
Poehnlein, Martin ;
Ulrich, Jonas ;
Kirschhoefer, Frank ;
Nusser, Michael ;
Muhle-Goll, Claudia ;
Kannengiesser, Bastian ;
Brenner-Weiss, Gerald ;
Luy, Burkhard ;
Liese, Andreas ;
Syldatk, Christoph ;
Hausmann, Rudolf .
EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY, 2015, 117 (02) :161-166
[29]   Lipase-catalyzed synthesis of aromatic polyesters [J].
Wu, XY ;
Linko, YY ;
Seppala, J ;
Leisola, M ;
Linko, P .
JOURNAL OF INDUSTRIAL MICROBIOLOGY & BIOTECHNOLOGY, 1998, 20 (06) :328-332
[30]   Progress of Lipase-Catalyzed Ester Synthesis in Ionic Liquid [J].
Li, Jing ;
Wang, Jun ;
Zhang, Leixia ;
Gu, Shuangshuang ;
Wu, Fuan ;
Guo, Yuewei .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (07) :1186-1194