Enzyme‐catalyzed regioselective synthesis of sugar esters and related compounds

Abstract

In this review, a comprehensive and illustrative survey is made of the regioselective synthesis of esters of sugars and related compounds using lipases. The main emphasis has been given to the screening and use of commercially available lipases for the enzymatic esterification of neutral monosaccharides, disaccharides, sugar alcohols and their selected ether and ester derivatives. The effect of solvents and solubilizing agents in improving the yields of the resultant sugar fatty acid esters has been incorporated. Further, solvent-free esterification with molten fatty acids, use of ionic liquids and microwave radiations for improvement in the methodology have also been discussed.

New Frontiers in Materials Science Opened by Ionic Liquids

“…Similar results have been reported for other IL systems as well. [30] Some ILs with lipase may be ideal media for expediting organic synthesis and such ILs have good prospects for the future in our opinion.…”

Development of a Karplus equation for 3JCOCH in ester-functionalized glucopyranoses and methylglucuronate.

“…A number of enzymatic and non-enzymatic methods for regioselective acetylation of unprotected or partially protected carbohydrates have been discussed in the literature. [16][17][18][19] Nevertheless, several attempts at regioselective acetylation using established non-enzymatic methods or adaptations thereof failed using unprotected glucose, despite their demonstrated success with methyl D-glucopyranoside. 18,20 The transformation was instead successful following a less direct synthetic route.…”

Chemoenzymatic synthesis: a strategy to obtain xylitol monoesters

“…3,4 Lipases display catalytic activity towards a large variety of alcohols and acids in ester synthesis reactions. 5,6 However, the esterification of sugar and fatty acid using lipases is hampered by the low solubility of sugars in most organic solvents, 7 thus making it difficult to choose the appropriate conditions to perform the reaction. 8 In addition, difficulties in controlling a specific degree of regio-esterification have been another limitation in this biocatalysis.…”

“…8 In addition, difficulties in controlling a specific degree of regio-esterification have been another limitation in this biocatalysis. 7 For the synthesis of xylitol monoesters acylated on the primary hydroxyl group, the control of regioselectivity in acylation reactions is a critical issue. 9 To overcome such limitations, the literature suggests several strategies such as solvent engineering, use of transesterification reaction instead of direct esterification or modification of the sugar structure.…”