Chemoenzymatic synthesis of homogeneous chondroitin polymers and its derivatives. (15th March 2020)

• Record Type: Journal Article
• Authors: Wang, Yaqian; Li, Shuang; Xu, Xuan; Tan, Yujie; Liu, Xian-wei; Fang, Junqiang
• Is Part Of: Carbohydrate polymers. Volume 232(2020)
• Publication Date: 2020-03-15
• Subjects: Chondroitin -- Zwitterionic polysaccharides -- N-sulfonation chondroitin; Polysaccharides -- Periodicals; Polysaccharides -- Periodicals; Polysaccharides -- Périodiques; Electronic journals; 547.78
• DOI: 10.1016/j.carbpol.2019.115822
• Languages: English
• ISSNs: 0144-8617

Abstract

Highlights: Report a chemoenzymatic strategy to generate homogeneous chondroitin polymers. Trisaccharide was the key factor for homogeneous chondroitin polymers synthesis. Zwitterionic and N -sulfonated chondroitin polymers were further synthesized. Abstract: Chondroitin sulfate is a linear glycosaminoglycan widely distributed as an important extracellular matrix component of mammalian cells. It participates in numerous pathological processes, however, illustration of its diverse biological roles is hampered by the unavailability of structurally defined chondroitin polymers and their derivatives. Herein, we report a novel homogeneous chondroitin polymers synthetic strategy which combines stepwise oligosaccharides synthesis with one-pot homogeneous chondroitin chain polymerization. Exogenous trisaccharide was proved to be the necessary acceptor for PmCS-catalyzed homogeneous chondroitin polymers synthetic reactions. The strategy exhibited a well-controlled relationship between the final sugar chain length and the molar ratios of reaction substrates that could synthesize homogenous chondroitin polymers with unprecedented narrow molecular weight distribution. More importantly, the strategy was further expanded to synthesis of unnatural zwitterionic and N -sulfonated chondroitin polymers by incorporation of sugar nucleotide derivatives into the synthetic approach.