Enzyme‐catalyzed regioselective synthesis of sucrose‐based esters

Abstract

Sucrose-based esters are nonionic biosurfactants, which can be synthesized from the enzyme-catalyzed esterification/transesterification of sucrose. The multi-hydroxyl groups of sucrose and the immiscibility of sucrose with the acyl donors are the main bottlenecks in obtaining highly regioselective sucrose-based esters. In this mini-review, the effects of reaction conditions such as biocatalysts, design of solvent systems used as reaction media, modification and denaturation of substrates, and coupling with external auxiliary physical fields such as microwave irradiation and ultrasonic waves on the yield of sucrose esters and regioselectivity of products are highlighted. The existing problems in the field of enzymatic synthesis of sucrose esters as well as its future perspectives were pointed out.

Enzymatic synthesis of new C-6-acylated derivatives of NAG-thiazoline and evaluation of their inhibitor activities towards fungal β-N-acetylhexosaminidase

“…Recently this methodology has been exploited for the transesterification of saccharides with long chain fatty acids as biodegradable emulsifiers [3][4][5] and regioselective acylation at 5 -OH of the monosaccharide prodrug of 5-fluorouridin [6]. Moreover, Novozym 435 (lipase from Candida antarctica immobilized on acrylic resin) has been successfully applied in the two-step regioselective synthesis of C-6 hybrid modified glycosides, e.g.…”

Biocatalysis and Biomass Conversion in Alternative Reaction Media

“…In particular, sucrose fatty acid esters find many applicationsi nf ood and cosmetics, [91] for example, as an emulsifier.T hey are currently manufactured by ac hemical process at elevatedt emperatures, resulting in low selectivities and side reactions affording colored impurities. In addition to being derived from renewable raw materials, they are tasteless, odorless, nontoxic, non-irritant, biodegradable, and have ah ydrophilic-lipophilic balance( HLB) that is tunable by as uitable choice of fatty acid and carbohydrate.…”

ChemInform Abstract: Biocatalysis and Biomass Conversion in Alternative Reaction Media

“…In addition to being derived from renewable raw materials, they are tasteless, odorless, nontoxic, non-irritant, biodegradable, and have ah ydrophilic-lipophilic balance( HLB) that is tunable by as uitable choice of fatty acid and carbohydrate. In particular, sucrose fatty acid esters find many applicationsi nf ood and cosmetics, [91] for example, as an emulsifier.T hey are currently manufactured by ac hemical process at elevatedt emperatures, resulting in low selectivities and side reactions affording colored impurities. Hence,t here is increasinginterestinenzymaticalternatives that can be conducted under milder conditions with highers electivities and higher product qualities.…”