Sulfation of arabinogalactan by sulfamic acid in dioxane

Vasil’eva, Natalia Yu.; Levdansky, Alexander V.; Кузнецов, Б. Н.; Skvortsova, Galina P.; Kazachenko, Аleksandr S.; Djakovitch, Laurent; Pinel, Catherine

doi:10.1134/s1068162015070158

Cited by 23 publications

(19 citation statements)

References 2 publications

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“…Sulfamic acid is a stable, non-hygroscopic and solid sulfating agent that has been used in the esterification of alcohols. [25,26] Compared with aggressive sulfuric or chlorosulfonic acid, sulfamic acid is milder and easier to handle. However, owing to the high melting point (ca.…”

Section: Anionization Of Sawdust In Desmentioning

confidence: 99%

“…Nevertheless, the presence of urea can improve its sulfation efficiency and reduce the reaction temperature. [25] Therefore, a strategy using sulfamic acid and urea to form an effective DES (through a hydrogen bonding interaction [17]) was schemed. [28] In the current study, sulfamic acid, applied as part of reactive DES, reacts with OH groups of sawdust forming corresponding ammonium salt of sulfate ester (Scheme 1).…”

Section: Anionization Of Sawdust In Desmentioning

confidence: 99%

“…Conventionally, sulfation of lignocellulosic biomass using sulfamic acid usually requires additional medium (e.g. dioxane, [25] N,N-Dimethylformamide and diglyme [26]), which can cause chemical pollution and waste during the preparation of sulfated biomaterials. [27] Nevertheless, sulfamic acid composed DES was reported for sulfation of cellulose without using any external solvent.…”

Section: Introductionmentioning

confidence: 99%

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Preparation of flame-retardant lignin-containing wood nanofibers using a high-consistency mechano-chemical pretreatment

Sirviö

Hong

Ämmälä

et al. 2019

Chemical Engineering Journal

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Highlights Mechano-chemical pretreatment was developed to produce anionic wood nanofiber. Deep eutectic solvent worked both as reactive agent and medium for the reaction. The reaction consistency of wood biomass was greatly improved (up to 60 wt%). Anionic wood nanofibers obtained high sulfate group contents (up to 3.1 mmol g -1 ). Multi-functional films can be fabricated from anionic wood nanofibers.ASNFs was obtained with high sulfate group contents (up to 3.1 mmol g -1 ). Besides, the ASNFs possessed a well-individualized structure with a homogeneous size distribution (3-5 nm in width). More importantly, films fabricated from ASNFs achieved strong flame resistance and good mechanical strength. Due to the presence of lignin, ASNF films were able to block over 90% of UV light (at a wavelength of 200-400 nm). The investigated functionalities of ASNFs led the lignocellulosic biomass residuals to be converted to high value-added bioproducts.Therefore, the reactive DES treatment combined with milling and heating process offers a practical and sustainable route for multi-functional biomaterial production, which can be potentially utilized, even at an industrial scale.

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Section: Anionization Of Sawdust In Desmentioning

confidence: 99%

Section: Anionization Of Sawdust In Desmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Preparation of flame-retardant lignin-containing wood nanofibers using a high-consistency mechano-chemical pretreatment

Sirviö

Hong

Ämmälä

et al. 2019

Chemical Engineering Journal

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“…Comparing with the IR spectra of these two polysaccharide, we found two strong absorption bands at 1259.85 cm −1 and 844.75 cm −1 of ACW0-Sul, which were attributed to S=O and C-O-S stretching vibration according to previous reported literature [ 36 ]. It is known that substituents such as sulfate groups cause regular shifts in the 13 C NMR spectrum of signals of the nearest carbon atoms [ 37 ]. Hence, determination of the location of these substituents is possible.…”

Section: Resultsmentioning

confidence: 99%

A Novel Heterogalactan from Antrodia camphorata and Anti-Angiogenic Activity of Its Sulfated Derivative

Ding

et al. 2017

Polymers

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A heterogalactan, named ACW0, was extracted from Antrodia camphorata and purified by anion exchange and gel permeation chromatography. It was composed of galactose (94.98%), traces of mannose (2.41%), and fucose (2.61%), with its molecular weight estimated to be 13.5 k Da. The polysaccharide ACW0 was shown to be a mannofucogalactan with a backbone chain of α-D-1,6-linked Gal, attached by a non-reducing terminal α-D-Man and α-L-Fuc on C-2 of nearly every six α-D-1,6-linked Gal residues. A sulfated polysaccharide, ACW0-Sul was achieved by the chlorosulfonic acid-pyridine method. Compared with the native polysaccharide, ACW0-Sul could disrupt tube formation and migration as well as cell growth of human microvascular endothelial cells (HMEC-1) dose-dependently. Further studies revealed that phosphorylation of Extracellular Regulated Protein Kinases (Erk) and Focal Adhesion Kinase (FAK) were significantly inhibited by ACW0-Sul. These results suggested that ACW0-Sul could be a potent candidate for anti-angiogenic agent development.

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“…produced by "Khimia drevesiny" (Irkutsk, Russia) under the name of "FibrolarS" was taken as a raw material. The samples with different sulphur contents (3.2; 5.1, 9.4 wt.%) were obtained by sulphating of arabinogalactan using sulphamic acid-urea complex method (Vasil'eva et al 2015), which is based on the reaction of sulphamic acid and urea in 1,4-dioxane. IR spectra of arabinogalactan and its sulphation products were phased out using Tensor-27 FT-IR spectrometer (Bruker, Germany) in the wavelength range of 400-4000 cm -1 .…”

Section: Methodsmentioning

confidence: 99%

Theoretical DFT interpretation of infrared spectra of biologically active arabinogalactan sulphated derivatives

et al. 2020

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Arabinogalactan (AG) and sulphated arabinogalactans (SAG) which are products of chemical modification of arabinogalactan polysaccharide with anticoagulant properties were studied by experimental infrared (IR) spectroscopy combined with density functional theory simulations. Mutual analythis of experimental and theoretical IR frequencies indicates that the descripancies between experiment and theory is caused by the influence of -OH groups, which led to the energy shift and broadening of the absorption IR bands. It was found that theoretical and experimental spectra correspond well within 3000-4000 cm -1 spectral region. Addition of sulphur group in AG structure causes hydroxyl group to become accessible for further sulphation. The difference between experimental and theoretical IR frequencies of sulphated AG derivatives is greater than for the parent arabinogalactan due to increase in the number of possible isomers and conformers.

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Sulfation of arabinogalactan by sulfamic acid in dioxane

Cited by 23 publications

References 2 publications

Preparation of flame-retardant lignin-containing wood nanofibers using a high-consistency mechano-chemical pretreatment

Preparation of flame-retardant lignin-containing wood nanofibers using a high-consistency mechano-chemical pretreatment

A Novel Heterogalactan from Antrodia camphorata and Anti-Angiogenic Activity of Its Sulfated Derivative

Theoretical DFT interpretation of infrared spectra of biologically active arabinogalactan sulphated derivatives

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