Enzymatic synthesis of amino sugar fatty acid esters

Abstract

N-Acetyl-glucosamine fatty acid esters were synthesized by a lipase-catalyzed transesterification with methyl hexanoate and N-acetyl-glucosamine (GlcNAc), which resulted in the formation of 2-(acetylamino)-2-deoxy-6-O-hexanoate-D-glucose, a novel glycolipid. Additionally N-butyryl-glucosamine (GlcNBu) was used for a similar synthesis, leading to the formation of 2-(butyrylamino)-2-deoxy-6-O-hexanoate-D-glucose. The higher hydrophobicity of GlcNBu led to an increase in the overall yield and the initial reaction rate when compared to the reaction with GlcNAc. By pre-dissolving GlcNAc and GlcNBu in dimethyl sulfoxide (DMSO), it was possible to completely dissolve both sugars in the organic solvent, thus further enhancing the initial reaction rate and yield respectively.Practical applications: Glycolipids are used in a wide range of applications, ranging from food, cosmetic, and pharmaceutical formulations, where they can be used as emulsifiers or foaming agents to classic cleaning products, utilizing their good detergent properties. Further applications may include fields like membrane protein extraction, bioremediation, or tertiary oil recovery. Novel glycolipids with tailor-made properties might be useful to improve any of the named applications and widen the diversity of available environmentally friendly surfactants, often termed "green surfactants." Glycolipids are the most prominent example therefrom.

Aspergillus oryzae lipase-catalyzed synthesis of glucose laurate with excellent productivity

“…2) to 64.5 %. Moreover, the productivity obtained in our optimized system is also much higher than others reported in literature (Ferrer et al 2000(Ferrer et al , 2005Ikeda and Klibanov 1993;Pöhnlein et al 2014;Yan et al 1999) (Table 2). It has to be noted, however, that the optimal reaction temperature may not have been reached within the range tested in this study (50-70 °C).…”

“…The synthetic reaction is normally performed in an organic solvent such as tert-butanol and 2-methyl-2-butanol (2M2B) (Ferrer et al 2000(Ferrer et al , 2005Ye and Hayes 2014;Gumel et al 2011;Kobayashi 2011;Ikeda and Klibanov 1993;Flores et al 2002;Pöhnlein et al 2014;Walsh et al 2009;Cao et al 1996).…”

“…In terms of enzyme selection, among different lipases (EC 3.1.1.3) that have been tested, Novozym 435 from Novozyme (Candida antarctica lipase B immobilized on acrylic resin) is the most popular one for catalyzing sugar Open Access *Correspondence: zyang@szu.edu.cn 1 College of Life Sciences, Shenzhen Key Laboratory of Microbial Genetic Engineering, Shenzhen University, Shenzhen 518060, Guangdong, China Full list of author information is available at the end of the article ester synthesis (Ferrer et al 2005;Ye and Hayes 2014;Gumel et al 2011;Kobayashi 2011;Flores et al 2002;Pöhnlein et al 2014;Cao et al 1996;Lin et al 2015). It is necessary to search for some other lipases that are cheap and catalytically efficient for this application.…”

Enzymatic synthesis and modification of surface‐active glycolipids

“…Starting in the 1980s with Klibanov and co‐workers showing the synthetic activity of lipases in water‐free organic solvents, numerous experiments have been performed to synthesize different glycolipids via various enzymatic routes. Substrates were amongst others monosaccharides (e.g., glucose , mannose galactose or N‐acetyl glucosamine ), di‐ and trisaccharides (e.g., saccharose , fructose , lactose or maltose ) to oligo‐ and polysaccharides like starch, cellulose and pectin .…”

Enzymatic synthesis and self-assembly of glycolipids: robust self-healing and wound closure performance of assembled soft materials

“…Generally, enzyme-triggered reactions are desirable for the precise synthesis of glycolipids under mild reaction conditions, with control in stereo-and regioselectivities, structure, substrate and functional groups. [33][34][35][36] Furthermore, enzymatic reactions display high catalytic efficiency and simple workup process either by ltration or centrifugation. [37][38][39] For the synthesis of acylated sugar, immobilized form of Candida antarctica lipase B (CALB), 40 Novozyme 435® is the best option because of its potential catalytic activity towards polyol ester of fatty acid synthesis, reusability, thermal stability and stable catalytic performance under various conditions.…”