An Integrated Enzymatic Approach to Produce Pentyl Xylosides and Glucose/Xylose Laurate Esters From Wheat Bran.

Chloé Jocquel,Murielle Muzard,Richard Plantier-Royon,Caroline Rémond

doi:10.3389/fbioe.2021.647442

Abstract

Alkyl glycosides and sugars esters are non-ionic surfactants of interest for various applications (cosmetics, food, detergency,…). In the present study, xylans and cellulose from wheat bran were enzymatically converted into pentyl xylosides and glucose and xylose laurate monoesters. Transglycosylation reaction catalyzed by the commercial enzymatic cocktail Cellic Ctec2 in the presence of pentanol led to the synthesis of pentyl β-D-xylosides from DP1 to 3 with an overall yield of 520 mg/g of xylans present in wheat bran. Enzymatic hydrolysis of wheat bran with Cellic Ctec2 and subsequent acylation of the recovered D-glucose and D-xylose catalyzed by the commercial lipase N435 in the presence of lauric acid or methyl laurate produced one D-glucose laurate monoester and one D-xylose laurate monoester. An integrated approach combining transglycosylation and (trans)esterification reactions was successfully developed to produce both pentyl xylosides and D-glucose and D-xylose laurate esters from the same batch of wheat bran.

Highlights

Surfactants include a large family of amphiphilic compounds exhibiting multiple properties as solubilizing agents, foaming agents, wetting agents, dispersants or emulsifiers depending on their composition and structure
Transglycosylation reactions were catalyzed by the enzyme Cellic Ctec2 (50 xylanase IU/mL) in the presence of Wheat bran (WB) (5%, w/v) and 50% pentanol in water (v/v) at 50◦C during 48 h with magnetic stirring (400 rpm)
TLC analysis allowed the visualization of pentyl xylosides from DP1 to 3 indicating that the xylanase activity of Cellic Ctec2 was able to catalyze transglycosylation reactions (Figure 2)

Summary

Introduction

Surfactants include a large family of amphiphilic compounds exhibiting multiple properties as solubilizing agents, foaming agents, wetting agents, dispersants or emulsifiers depending on their composition and structure. Short aliphatic chains lead to hydrotropic properties which can be useful for detergency or as foam boosters in cosmetics (von Rybinski and Hill, 1998; Bouxin et al, 2010). These surfactants are Enzymatic Production of Biosurfactants worldwide produced at a scale of 100,000–200,000 tons per year (Jerome et al, 2018). Chemical routes requiring the use of polar solvents, a catalyst and high reaction temperatures are used for the formation of fatty acid esters by esterification or transesterification reactions (Polat and Linhardt, 2001) These chemical syntheses generally lead to complex mixtures of monoesters, di- and higher esters and to different regioisomers

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