Abstract
Environmentally friendly and biodegradable reaction media are an important part of a sustainable glycolipid production in the transition to green chemistry. Deep eutectic solvents (DESs) are an ecofriendly alternative to organic solvents. So far, only hydrophilic DESs were considered for enzymatic glycolipid synthesis. In this study, a hydrophobic DES consisting of (-)-menthol and decanoic acid is presented for the first time as an alternative to hydrophilic DES. The yields in the newly introduced hydrophobic DES are significantly higher than in hydrophilic DESs. Different reaction parameters were investigated to optimize the synthesis further. Twenty milligrams per milliliter iCalB and 0.5 M glucose resulted in the highest initial reaction velocity for the esterification reaction, while the highest initial reaction velocity was achieved with 1.5 M glucose in the transesterification reaction. The enzyme was proven to be reusable for at least five cycles without significant loss of activity.
Highlights
Surfactants are amphiphilic molecules that are applied in numerous industries and in personal care on a daily basis and a multimillion-ton scale per year [1,2,3,4]
While microbial fermentation is limited to certain molecules, chemical and enzymatical synthesis can be used for tailor-made glycolipid synthesis with theoretically no restriction regarding sugar moiety and alkyl chain
The main purpose of this study was to examine the suitability of a hydrophobic (-)-menthol: 2. Results decanoic acid Deep eutectic solvents (DESs) as a medium for glycolipid synthesis and to compare the results with the synthesis
Summary
Surfactants are amphiphilic molecules that are applied in numerous industries and in personal care on a daily basis and a multimillion-ton scale per year [1,2,3,4]. Glycolipids, consisting of a sugar moiety acylated with an alkyl chain, are the biggest group within the biosurfactants. They are characterized by properties similar or even superior to their petrochemical counterparts while being biodegradable, non-toxic and skin-friendly [5,6,7]. Glycolipids can be synthesized by microbial fermentation, e.g., sophorose lipids and rhamnolipids, by chemical or enzymatic synthesis [8,9]. While microbial fermentation is limited to certain molecules, chemical and enzymatical synthesis can be used for tailor-made glycolipid synthesis with theoretically no restriction regarding sugar moiety and alkyl chain. For the linkage of saccharide and alkyl chain, a reaction solvent of low water activity is needed as reversed hydrolysis only occurs under conditions of reduced water activity [10,11,12]
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