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    Regioselective synthesis of 6''-O-lauroyl-1-kestose and 6'''-O-lauroylnystose by sequential enzymatic reactions of transfructosylation and acylation

    Year: 2022

    Journal: Biocatal. Biotransform., Volume 40, MAR 4, page 133–143

    Authors: Roberto Campos-Valdez, Amador; Casas-Godoy, Leticia; Sandoval, Georgina; Hernandez, Lazaro; Lanzi Sassaki, Guilherme; Alencar de Menezes, Leociley Rocha; Campos-Teran, Jose; Reyes-Duarte, Dolores; Arrizon, Javier

    Organizations: LIBBA laboratory and Industrial Biotechnology Unit of CIATEJ; CONACYT (Mexico) [268290]; CNPq [430922/2018-3, 303352/2017-5]; UFPR - Rede de Internacionalizacao em Bioprospeccao, Biogeoquimica e Biotecnologia Ambiental [CAPES-PrInt] [88887.311742/2018-00]; FINEP; UFPR NMR Center

    Keywords: Transfructosylation; fructooligosaccharides; acylation; sequential enzymatic process; sugar esters

    Fructan fatty acid esters are amphiphilic compounds with potential applications in the food industry due to their surface-active properties on the air/water interface. In this work, the regioselective synthesis of fatty acid esters of short-chain inulin-type fructooligosaccharides (FOS) was carried out in a two-step process comprising sequential enzymatic reactions of transfructosylation and acylation. In the first step, Schedonorus arundinaceus sucrose:sucrose 1-fructosyltransferase (1-SST, EC 2.4.1.99) converted sucrose (600 g/L) into the trisaccharide 1-kestose and the tetrasaccharide nystose in a ratio 9:1 with their sum accounting for 53% (w/w) of total carbohydrates. In the second step, the FOS mixture was transesterified with vinyl laurate in 2-methyl-2-butanol by immobilized Candida antarctica lipase B (CALB) (EC.3.1.1.3). NMR analysis of the synthesized monolaurate FOS esters revealed a regioselective acylation of the 6-OH of the terminal fructosyl moiety of both 1-kestose and nystose. The hydrophilic-lipophilic balance (HLB) values of 6''-O-lauroyl-1-kestose and 6'''-O-lauroylnystose were 14.7 and 15.7, respectively; which suggests their use as oil in water (O/W) emulsifiers. The main compound 6''-O-lauroyl-1-kestose with critical micelle concentration (CMC) of 0.6 mM and surface tension of 45.8 mN/m proved to be a more efficient surfactant than 6'''-O-lauroylnystose (CMC 5.38 mM) and surface tension 36.26 mN/m). We report a regioselective method for the synthesis of lauryl-FOS using the abundant and renewable resource sucrose as the starting substrate.
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