Flow synthesis, characterization, anticoagulant activity of xylan sulfate from sugarcane bagasse

Chen, Yanjun; Sun, Xiangxiang; Shan, Junqiang; Tang, Chenglun; Hu, Ruijia; Shen, Tao; Qiao, Hongqun; Li, Ming; Zhuang, Wei; Zhu, Chenjie; Ying, Hanjie

doi:10.1016/j.ijbiomac.2019.11.124

Cited by 18 publications

(10 citation statements)

References 37 publications

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“…Recently, several methods for synthesizing the sulfated derivatives of polysaccharides on the basis of a new approach have been proposed. In particular, Chen et al described a new method for sulfation of xylan in a flow-through unit and investigated its anticoagulant activity. In ref , xylan was treated with the NaBH 4 reducing agent, which enhanced the purity of the product.…”

Section: Introductionmentioning

confidence: 99%

Sulfation of Diethylaminoethyl-Cellulose: QTAIM Topological Analysis and Experimental and DFT Studies of the Properties

et al. 2021

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Sulfated cellulose derivatives are biologically active substances with anticoagulant properties. In this study, a new sulfated diethylaminoethyl (DEAE)-cellulose derivative has been obtained. The effect of a solvent on the sulfation process has been investigated. It is shown that 1,4-dioxane is the most effective solvent, which ensures the highest sulfur content in DEAE-cellulose sulfate under sulfamic acid sulfation. The processes of sulfamic acid sulfation in the presence of urea in 1,4-dioxane and in a deep eutectic solvent representing a mixture of sulfamic acid and urea have been compared. It is demonstrated that the use of 1,4-dioxane yields the sulfated product with a higher sulfur content. The obtained sulfated DEAE-cellulose derivatives have been analyzed by Fourier transform infrared spectroscopy, X-ray diffractometry, and scanning electron and atomic force microscopy, and the degree of their polymerization has been determined. The introduction of a sulfate group has been confirmed by the Fourier transform infrared spectroscopy data; the absorption bands corresponding to sulfate groups have been observed in the ranges of 1247–1256 and 809–816 cm–1. It is shown that the use of a deep eutectic solvent leads to the side carbamation reactions. Amorphization of DEAE-cellulose during sulfation has been demonstrated using X-ray diffractometry. The geometric structure of a molecule in the ground state has been calculated using the density functional theory with the B3LYP/6-31G(d, p) basis set. The reactive areas of DEAE-cellulose and its sulfated derivatives have been analyzed using molecular electrostatic potential maps. The thermodynamic parameters (heat capacity, entropy, and enthalpy) of the target sulfation products have been determined. The HOMO–LUMO energy gap, Mulliken atomic charges, and electron density topology of the title compound have been calculated within the atoms in molecule theory.

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Section: Introductionmentioning

confidence: 99%

Sulfation of Diethylaminoethyl-Cellulose: QTAIM Topological Analysis and Experimental and DFT Studies of the Properties

et al. 2021

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“…The low‐frequency band with a maximum at 583 cm −1 is related to bending vibrations of δ (O=S=O). Moreover, a decrease in the intensity of the C−OH absorption band at 2922 and 1047 cm −1 in the sulfated xylan spectrum as compared with the case of xylan indicates substitution of most hydroxyl groups [18] …”

Section: Resultsmentioning

confidence: 98%

“…Mannose (1.52 %), glucose (1.48 %), galactose (0.97 %), and arabinose (0.89 %) appeared as minor components. The arabinose‐to‐xylose ratio reflects the degree of branching or linearity of polysaccharides [18] . The arabinose‐to‐xylose ratio in xylan isolated from birch wood holocellulose (0.01) suggests a high degree of polymerization of the basic component (xylan) with fewer links to other monosaccharide components.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, a decrease in the intensity of the CÀ OH absorption band at 2922 and 1047 cm À 1 in the sulfated xylan spectrum as compared with the case of xylan indicates substitution of most hydroxyl groups. [18] To study the structure of xylan sulfates, the authors of [13,16,17] used the fullrange of NMR experiments ( 1 H NMR, 13 C NMR, 1 HÀ 1 H COSY, 1 HÀ 13 C HSQC, etc.). The chemical shifts of H and C atoms of the main β-D-xylopyranose units of xylan sulfates with different contents of sulfate groups were determined.…”

Section: Characterization Of Xylan Sulfatementioning

confidence: 99%

“…These results are in good agreement with the literary data. In, [13] it was shown by the 13 C NMR method that the chemical shifts of C1-C5 atoms in the elementary chain of β-1,4-xylan appear at 102.4, 72.8, 73.7, 76.4, and 63.0 ppm, respectively, and, in, [18] they appeared at 102.4, 73.4, 75.1, 75.8, and 63.3 ppm, respectively.…”

Section: Characterization Of Xylan Isolated From Birch Wood Holocellu...mentioning

confidence: 99%

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Synthesis of Birch Wood Xylan Sulfate in the Sulfamic Acid–Urea Melt

Levdansky,

Garyntseva,

Levdansky

2023

ChemistrySelect

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The synthesis of polysaccharide sulfates without harmful solvents used is a serious environmental problem. A method for the synthesis of xylan sulfate using the sulfamic acid–urea melt as a sulfating agent without solvents is proposed. The melt is prepared by heating the sulfamic acid–urea mixture with a molar ratio of 1 : 1 at a temperature of 110 °C. This ratio allows significant reduction of side reactions, in particular, carbamation of xylan. Sulfation is carried out at temperatures of 110,115, 120, 125, and 130 °C. The maximum yield and degree of substitution (DSsulfate 1.40) are attained at atemperature of 115 °C. The proposed method makes it possible to synthesize xylan sulfate rapidly (for 0.5 h) and without contamination of the obtained product with toxic solvents, e. g., dimethyl sulfoxide, pyridine, etc. The composition and structure of initial and sulfated xylan are confirmed by FTIR, NMR, GC, and elemental analysis.

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Analytical Techniques Applied to Hemicellulose Structure and Functional Characterization

Melati

Freitas

Brienzo

2022

Clean Energy Production Technologies

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Flow synthesis, characterization, anticoagulant activity of xylan sulfate from sugarcane bagasse

Cited by 18 publications

References 37 publications

Sulfation of Diethylaminoethyl-Cellulose: QTAIM Topological Analysis and Experimental and DFT Studies of the Properties

Sulfation of Diethylaminoethyl-Cellulose: QTAIM Topological Analysis and Experimental and DFT Studies of the Properties

Synthesis of Birch Wood Xylan Sulfate in the Sulfamic Acid–Urea Melt

Analytical Techniques Applied to Hemicellulose Structure and Functional Characterization

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