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Chemoenzymatic synthesis of homogeneous chondroitin polymers and its derivatives.
Carbohydrate Polymers ( IF 10.7 ) Pub Date : 2019-12-31 , DOI: 10.1016/j.carbpol.2019.115822
Yaqian Wang 1 , Shuang Li 1 , Xuan Xu 1 , Yujie Tan 1 , Xian-Wei Liu 1 , Junqiang Fang 1
Affiliation  

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.

中文翻译:

化学酶促合成均质软骨素聚合物及其衍生物。

硫酸软骨素是一种线性的糖胺聚糖,广泛分布为哺乳动物细胞的重要细胞外基质成分。它参与了许多病理过程,但是,由于缺乏结构确定的软骨素聚合物及其衍生物,阻碍了其多种生物学作用的说明。在这里,我们报告了一种新颖的均质软骨素聚合物合成策略,该策略将逐步寡糖合成与一锅均质软骨素链聚合相结合。事实证明,外源三糖是PmCS催化的均质软骨素聚合物合成反应的必需受体。该策略在最终糖链长度和反应底物的摩尔比之间显示出可控的关系,该反应底物可以合成具有前所未有的窄分子量分布的均质软骨素聚合物。更重要的是,通过将糖核苷酸衍生物掺入到合成方法中,该策略进一步扩展到合成非天然两性离子和N-磺化软骨素聚合物。
更新日期:2019-12-31
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