Enzymatic synthesis of alkyl β-d-xylosides and oligoxylosides from xylans and from hydrothermally pretreated wheat bran

Ochs, Marjorie; Muzard, Murielle; Plantier‐Royon, Richard; Estrine, Boris; Rémond, Caroline

doi:10.1039/c1gc15719a

Cited by 43 publications

(49 citation statements)

References 38 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Various starting materials, including agricultural residues (such as sugarcane bagasse, corn stover, wheat bran (WB) and wheat straw (WS)) and forest residues, represent biomass substrates of interest to biorefineries [2,3]. The development of integrated biorefineries requires valorizing the entire plant, and in this context, the transformation of hemicellulosic components of plant cell walls offers new opportunities for biorefineries to produce high value molecules, such as alkyl pentosides [4,5]. …”

Section: Introductionmentioning

confidence: 99%

The hemicellulolytic enzyme arsenal of Thermobacillus xylanilyticus depends on the composition of biomass used for growth

et al. 2012

Self Cite

View full text Add to dashboard Cite

BackgroundThermobacillus xylanilyticus is a thermophilic and highly xylanolytic bacterium. It produces robust and stable enzymes, including glycoside hydrolases and esterases, which are of special interest for the development of integrated biorefineries. To investigate the strategies used by T. xylanilyticus to fractionate plant cell walls, two agricultural by-products, wheat bran and straw (which differ in their chemical composition and tissue organization), were used in this study and compared with glucose and xylans. The ability of T. xylanilyticus to grow on these substrates was studied. When the bacteria used lignocellulosic biomass, the production of enzymes was evaluated and correlated with the initial composition of the biomass, as well as with the evolution of any residues during growth.ResultsOur results showed that T. xylanilyticus is not only able to use glucose and xylans as primary carbon sources but can also use wheat bran and straw. The chemical compositions of both lignocellulosic substrates were modified by T. xylanilyticus after growth. The bacteria were able to consume 49% and 20% of the total carbohydrates in bran and straw, respectively, after 24 h of growth. The phenolic and acetyl ester contents of these substrates were also altered. Bacterial growth on both lignocellulosic biomasses induced hemicellulolytic enzyme production, and xylanase was the primary enzyme secreted. Debranching activities were differentially produced, as esterase activities were more important to bacterial cultures grown on wheat straw; arabinofuranosidase production was significantly higher in bacterial cultures grown on wheat bran.ConclusionThis study provides insight into the ability of T. xylanilyticus to grow on abundant agricultural by-products, which are inexpensive carbon sources for enzyme production. The composition of the biomass upon which the bacteria grew influenced their growth, and differences in the biomass provided resulted in dissimilar enzyme production profiles. These results indicate the importance of using different biomass sources to encourage the production of specific enzymes.

show abstract

Section: Introductionmentioning

confidence: 99%

The hemicellulolytic enzyme arsenal of Thermobacillus xylanilyticus depends on the composition of biomass used for growth

et al. 2012

Self Cite

View full text Add to dashboard Cite

show abstract

“…As disclosed in the literature (Ochs et al, ), partitioning of octyl oligoxyloside between aqueous and octanol phase depends on the average degree of polymerization (DP), octyl β‐ d‐ xyloside (95%), octyl β‐ d‐ xylobioside (88%), and octyl β‐ d‐ xylotrioside (62%) were mainly localized in the octanol phase. The result could be considered as octyl β‐ d‐ xylopyranoside (HLB = 11.4 < 12.0) had very small water solubility (0.05 g per 100 g [water]) (Kuang et al, ), octyl β‐ d‐ xylobioside (HLB = 14.3) and octyl β‐ d‐ xylotrioside (HLB = 15.7) should have higher water solubility though the data were not found in literature, but the two anomeric pure alkyl oligoxylosides are more difficult to prepare than alkoxyethyl β‐ d‐ xyloside with glycochemistry.…”

Section: Resultsmentioning

confidence: 92%

“…Accordingly, APG based on xylose or xylan instead of glucose, maltose, and starch as raw material will be a potential hot research topic. Indeed, enzymatic/microbial, Koenigs-Knorr reaction or Fischer glycosylation reactions can be used to synthesis xylose-based surfactants that could be a useful class of xylose derivatives (Bouxin, Marinkovic, Bras, & Estrine, 2010;Chatron-Colliet et al, 2017;Damez et al, 2007;Das et al, 2017;Ochs, Muzard, Plantier-Royon, Estrine, & Rémond, 2011;Satgé, Bras, Hénin, & Muzart, 2005). Surface activity has been reported such as the surface tension of octyl β-D-xyloside and octyl α/β-D-xyloside was 30 and 27 mN m −1 , at their critical micelle concentration (CMC) (5.72 × 10 −2 and 3.63 × 10 −3 mol L −1 ), respectively Liew et al, 2015).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Properties of Alkoxyethyl β‐d‐Xylopyranoside

Shen

Chen

et al. 2018

J Surfact & Detergents

View full text Add to dashboard Cite

In order to improve the water solubility of sugar‐based surfactants, alkyl β‐d‐xylopyranosides, novel sugar‐based surfactants, 1,2‐trans alkoxyethyl β‐d‐xylopyranosides, with alkyl chain length n = 6–12 were stereoselectively prepared by the trichloroacetimidate method. Their properties including hydrophilic–lipophilic balance (HLB) number, water solubility, surface tension, emulsification, foamability, thermotropic liquid crystal, and hygroscopicity were investigated. The results indicated that their HLB number decreased with increase of alkyl chain, the water solubility improved since the hydrophilic oxyethene (─OCH2CH2─) fragment was introduced. The dissolution process was entropy driven at 25–45 °C for alkyl chain length n = 6–10. Octyloxyethyl β‐d‐xylopyranoside had the best foaming ability. Nonyloxyethyl β‐d‐xylopyranoside had the best foam stability and the emulsifying ability was better in toluene/water system than in rapeseed oil/water system. The surface tension of in aqueous solution dropped to 27.8 mN m−1 at the critical micelle concentration, and it also showed the most distinct thermotropic liquid phases with cross pattern texture upon heating and the fan schlieren texture on cooling. Hexyloxyethyl β‐d‐xylopyranoside possessed the strongest hygroscopicity. Based on the effective improvement of water solubility, the prepared alkoxyethyl β‐d‐xylopyranosides showed excellent surface activity and are expected to develop their practical application as a class of novel sugar‐based surfactants.

show abstract

“…The yield of alkyl xylosides were also very low and did not exceed 33%. As xylose source can be also used hemicellulose (pentosane‐rich lignocellulosic biomass) . Intensive study on the use of wheat straw pentosanes for the synthesis of alkyl xylosides was conducted by Estrine et al .…”

Section: Introductionmentioning

confidence: 99%

Micellar Route of the Synthesis of Alkyl Xylosides: An Unexpected Effect of Amphiphilic Imidazolium Ionic Liquids

et al. 2018

View full text Add to dashboard Cite

This manuscript presents results from the investigation on the synthesis of alkyl xylosides by the novel, very efficient and promising protocol of the Fischer synthesis from unprotected xylose and aliphatic alcohol. The use of 1‐alkyl‐3‐methylimidazolium hydrogen sulfate ionic liquids as the catalysts with dual functionality (surfactant + acid catalyst) and micellar reaction system are the main novelty of described method. It has been found that in developed method of the synthesis of alkyl xylosides the reaction of unprotected xylose with aliphatic alcohols carried out in mild reaction conditions and leads to alkyl xylosides with high yields. In progress analyses by Dynamic Light Scattering (DLS), High Performance Liquid Chromatography (HPLC) and Gas Chromatography (GC/MS) confirm the general postulated pathway of developed method.

show abstract

Enzymatic synthesis of alkyl β-d-xylosides and oligoxylosides from xylans and from hydrothermally pretreated wheat bran

Cited by 43 publications

References 38 publications

The hemicellulolytic enzyme arsenal of Thermobacillus xylanilyticus depends on the composition of biomass used for growth

The hemicellulolytic enzyme arsenal of Thermobacillus xylanilyticus depends on the composition of biomass used for growth

Synthesis and Properties of Alkoxyethyl β‐d‐Xylopyranoside

Micellar Route of the Synthesis of Alkyl Xylosides: An Unexpected Effect of Amphiphilic Imidazolium Ionic Liquids

Contact Info

Product

Resources

About