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• Review •

Enzyme-Catalyzed Regioselective Synthesis of Carbohydrate Fatty Acid Esters in Ionic Liquids

Shi Yugang1,2, Cai Yan3, Li Jianrong1, Chu Yenho2   

  1. 1. School of Food Science and Biotechnology, Zhejiang Gongshang University, Hangzhou 310035, China;
    2. Department of Chemistry and Biochemistry, National Chung Cheng University, Chia-Yi 621, China;
    3. School of Chemistry and Chemical Engineering, Nantong University, Nantong 226019, China
  • Received: Revised: Online: Published:
  • Contact: Shi Yugang E-mail:yugangshi@126.com
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Carbohydrate fatty acid esters (CFAE) are nonionic biosurfactants, which can be synthesized from the enzyme-catalyzed esterification/transesterification of carbohydrates. These esters are increasingly used as valuable commodity chemicals in food, pharmaceutical and cosmetic industries. In addition, some CFAE also show antitumor and/or antibiotic activities. CFAE could be prepared enzymatically under mild conditions with a high regioselectivity. Synthesis of CFAE in non-aqueous solvents is difficult due to the low solubility of carbohydrates. The multi-hydroxyl groups of carbohydrates and the immiscibility with the acyl group donor are the major obstacles in the CFAE synthesis process. Although traditional water-miscible organic solvents also enhance solubility, they often inactivate enzymes. However, ionic liquids do not even when they have similar polarities. The use of ionic liquids has offered many advantages to the biocatalysis field, including improved enzyme's activity and stability, and better substrate dissolution makes the initial acylation faster and makes the regioselective acylation of sugars higher. Ionic liquids may be greener than organic solvents because the reaction system can be reused/recycled. Here, the main factors (enzymes, the solubility of substrates in ILs, property of substrates) affecting the enzymatic reaction are introduced. The latest progress of research on enzymatic synthesis of CFAE in ionic liquids is reviewed. In addition, the existing problems in the field of enzymatic synthesis of CFAE as well as its future perspectives are pointed out.

Contents
1 Introduction
2 Enzymes for the synthesis of CFAE
2.1 Enzymes from different sources
2.2 The pretreatment of enzymes
3 Ionic liquids and carbohydrates
3.1 Ionic liquids
3.2 Ionic liquids that dissolve carbohydrates
4 Property of substrates
5 Enzymatic synthesis of CFAE in ionic liquids
5.1 Monosaccharides
5.2 Disaccharides
5.3 Polysaccharides
5.4 Other related compounds
6 Conclusion and future outlook

Key words: carbohydrate fatty acid esters, ionic liquids, enzymatic catalysis, regioselectivity

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