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

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

doi:10.1016/j.ijbiomac.2019.11.124

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

Int J Biol Macromol. 2020 Jul 15:155:1460-1467. doi: 10.1016/j.ijbiomac.2019.11.124. Epub 2019 Nov 14.

Authors

Yanjun Chen¹, Xiangxiang Sun², Junqiang Shan³, Chenglun Tang⁴, Ruijia Hu⁵, Tao Shen⁶, Hongqun Qiao⁷, Ming Li⁸, Wei Zhuang⁹, Chenjie Zhu¹⁰, Hanjie Ying¹¹

Affiliations

¹ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China. Electronic address: chenyj@njtech.edu.cn.
² College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China. Electronic address: sunxiangxing@njtech.edu.cn.
³ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China. Electronic address: sjq19920602@njtech.edu.cn.
⁴ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China. Electronic address: tangcl@njtech.edu.cn.
⁵ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China. Electronic address: huruijia@njtech.edu.cn.
⁶ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China. Electronic address: shentao@njtech.edu.cn.
⁷ Jiangsu Drug Safety Evaluation Center, Nanjing 211816, China. Electronic address: qiaohongqun@njtech.edu.cn.
⁸ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China. Electronic address: m.li@njtech.edu.cn.
⁹ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China; School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China. Electronic address: weizhuang@njtech.edu.cn.
¹⁰ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China; School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China. Electronic address: zhucj@njtech.edu.cn.
¹¹ College of Biotechnology and Pharmaceutical Engineering, Nanjing Tech University, Nanjing 211816, China; School of Chemical Engineering, Zhengzhou University, Zhengzhou 450001, China. Electronic address: yinghanjie@njtech.edu.cn.

PMID: 31734367
DOI: 10.1016/j.ijbiomac.2019.11.124

Abstract

High-value utilization of hemicellulose is critical to improve the append value of integrated biorefineries. In this research, the alkali-soluble sugarcane bagasse hemicellulose was sulfated using chlorosulfonic acid and N,N-dimethylformamide/LiCl under homogeneous conditions. With the aid of flow technique, a rapid, mild, and efficient method for the synthesis of xylan sulfate with high molecular weight and controllable degree of substitution was achieved. The results showed that the reaction time and the degradation of xylan chain were drastically reduced compared to the "in flask" batch conditions. High molecular weight of the product (M_w = 148,217) with a reasonable degree of substitution (DS = 1.49) could be obtained even at room temperature in 10 min under the present flow system. Anticoagulant experiments showed good anticoagulant activity of the resultant xylan sulfate, which could significantly prolong the activated partial thromboplastin time and thrombin time. This work not only provides a novel method for the synthesis of xylan sulfate, but also offers new opportunities for the production of other functional polysaccharide derivatives under the flow reaction conditions.

Keywords: Flow synthesis; Hemicellulose; Xylan sulfate.

MeSH terms

Anticoagulants / chemical synthesis
Anticoagulants / chemistry*
Anticoagulants / pharmacology*
Cellulose / chemistry*
Chemistry Techniques, Synthetic
Humans
Hydrogen-Ion Concentration
Molecular Weight
Pentosan Sulfuric Polyester / chemical synthesis
Pentosan Sulfuric Polyester / chemistry*
Pentosan Sulfuric Polyester / pharmacology*
Polysaccharides / chemistry
Saccharum / chemistry*
Solubility
Sulfonic Acids / chemistry

Substances

Anticoagulants
Polysaccharides
Sulfonic Acids
chlorosulfonic acid
Pentosan Sulfuric Polyester
hemicellulose
Cellulose
bagasse