Polar co-solvents in tertiary alcohols effect initial reaction rates and regio-isomeric ratio ranging from 1.2 to 2.2 in a lipase catalysed synthesis of 6-O- and 6′-O-stearoyl sucrose

Ritthitham, Sinthuwat; Wimmer, Reinhard; Pedersen, Lars Haastrup

doi:10.1016/j.procbio.2011.01.004

Cited by 8 publications

(6 citation statements)

References 35 publications

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“…The pervious literature has reported that the regioselectivity and yields of lipase‐catalyzed reactions were dependent on the nature of the organic solvent used . Several organic solvents of low toxicity in an aqueous two‐phase system were investigated in our research.…”

Section: Resultsmentioning

confidence: 99%

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Candida rugosa lipase‐catalyzed synthesis of sucrose‐6‐acetate in a 2‐butanol/buffer two‐phase system

Xiang

Qian

Liu

et al. 2013

Engineering in Life Sciences

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Sucrose‐6‐acetate, a short‐chain monoester, is an important intermediate for the preparation of sucralose. Regioselective transformations of mono‐ and oligosaccharides by enzymes have been performed in organic solvents. The present study was carried out with Candida rugosa lipase to synthesize sucrose‐6‐acetate by transesterification of sucrose and vinyl acetate in a two‐phase system consisting of a buffer solution and an organic solvent. The screening results revealed that 2‐butanol/Tris‐HCl was the optimal two‐phase system for biocatalysis, and other factors influencing the synthesis of sucrose‐6‐acetate were also studied. Three major factors (temperature, initial buffer pH, and molar ratio of substrates) were identified through Plackett–Burman design, and the response surface methodology was employed to optimize the reaction process. Under optimal conditions, the yield of sucrose‐6‐acetate reached up to 57.42%. The aqueous two‐phase system was successfully applied to the synthesis of sucrose‐6‐acetate with high yield, low toxicity, good resolution, low cost, and simple scale‐up.

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Section: Resultsmentioning

confidence: 99%

“…TLC detection was performed on silica gel plates using acetic ether/methanol (3:1 v/v) as the mobile phase . Reaction mixture spots were visualized by spraying with vaporized sulfuric acid/methanol (1:1 v/v) and then heating at 150°C for 5 min.…”

Section: Methodsmentioning

confidence: 99%

Candida rugosa lipase‐catalyzed synthesis of sucrose‐6‐acetate in a 2‐butanol/buffer two‐phase system

Xiang

Qian

Liu

et al. 2013

Engineering in Life Sciences

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“…This result could be attributed to the decrease in solubility into 2M2B when the DP of XOs increased from 2 to 4. DMSO was reported as an interesting co-solvent for acylation with lipases in 2M2B or tert-butanol as it can improve the solubility of oligosaccharides into an organic solvent [51,52]. DMSO was generally used at concentration lower than 20% in order to not generate the denaturation of lipases.…”

Section: Synthesis Of Xylo-oligosaccharide Estersmentioning

confidence: 99%

Enzymatically-synthesized xylo-oligosaccharides laurate esters as surfactants of interest

Gérard

Thomas

Muzard

et al. 2020

Carbohydrate Research

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Lipase-catalyzed synthesis of xylo-oligosaccharides esters from pure xylobiose, xylotriose and xylotetraose in the presence of vinyl laurate was investigated. The influence of different experimental parameters such as the loading of lipase, the reaction duration or the use of a co-solvent was studied and the reaction conditions were optimized with xylobiose. Under the best conditions, a regioselective esterification occurred to yield a monoester with the acyl chain at the OH-4 of the xylose unit at the non-reducing end. Surface-active properties of these pure xylo-oligosaccharides fatty esters have been evaluated. They display interesting surfactant activities that differ according to the degree of polymerization (DP) of the glycone moiety.

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“…1). [9][10][11] The present investigation aimed to further explore the physicochemical differences between the regioisomers and how the position of the fatty acid ester substitution affects the molecular and conformational stability. This was performed on the isolated compounds 6-and 6 -O-lauroyl sucrose by matrix-assisted laser desorption/ionization (MALDI) time-of-flight (TOF) mass spectrometry (MS), high-resolution Orbitrap mass spectrometry (HRMS), and electrospray-ionization (ESI) tandem mass spectrometry (MS/MS).…”

Section: Introductionmentioning

confidence: 99%

“…Chemical shifts (δ, ppm) from NMR spectroscopy analyses shown, confirming the ester substitution positions. [9][10][11] …”

Section: Introductionmentioning

confidence: 99%

Structural Analyses of Sucrose Laurate Regioisomers by Mass Spectrometry Techniques

Lie

Stensballe

Pedersen

2015

Journal of Carbohydrate Chemistry

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6-And 6 -O-lauroyl sucrose were isolated and analyzed by matrix-assisted laser desorption/ionisation (MALDI) time-of-flight (TOF) mass spectrometry (MS), Orbitrap high-resolution (HR) MS, and electrospray-ionization (ESI) tandem mass spectrometry (MS/MS). The analyses aimed to explore the physicochemical differences between the regioisomers and how the position of the fatty acid ester substitution affects the molecular and conformational stability. MALDI-TOF MS resulted in signals characteristic for the molecular ion adducts with sodium and potassium, [M + Na] + and [M + K] + , m/z 547.9 and 563.8, respectively, and Orbitrap HRMS confirmed the mass of [M + Na] + (m/z 547.2712). ESI-MS/MS on the precursor ion [M + Na] + resulted in product ion mass spectra showing two high-intensity signals for each sample. 6-O-Lauroyl sucrose produced signals located at m/z 547.27 and m/z 385.21, corresponding to the 6-O-lauroyl glucose sodium adduct ions, while the signals for 6 -O-lauroyl sucrose were located at m/z 385.22 and 367.20, respectively corresponding to the sodium adduct ions with 6-O-lauroyl fructose and 6-O-lauroyl fructosyl. The mass spectra of the two regioisomers were clearly different, and the investigation revealed the importance of the position of the fatty acid ester for the conformational stability and resulting fragmentation pathways of sucrose laurate regioisomers. The results of the employed MS techniques indicated the higher stability of the glycosidic linkage in 6-O-lauroyl sucrose, compared to the 6 -O-regioisomer.

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Polar co-solvents in tertiary alcohols effect initial reaction rates and regio-isomeric ratio ranging from 1.2 to 2.2 in a lipase catalysed synthesis of 6-O- and 6′-O-stearoyl sucrose

Cited by 8 publications

References 35 publications

Candida rugosa lipase‐catalyzed synthesis of sucrose‐6‐acetate in a 2‐butanol/buffer two‐phase system

Candida rugosa lipase‐catalyzed synthesis of sucrose‐6‐acetate in a 2‐butanol/buffer two‐phase system

Enzymatically-synthesized xylo-oligosaccharides laurate esters as surfactants of interest

Structural Analyses of Sucrose Laurate Regioisomers by Mass Spectrometry Techniques

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