Xiao Chunsheng, Zhao Changwen, He Pan, Tang Zhaohui, Chen Xuesi, Jing Xiabin
Key Laboratory of Polymer Ecomaterials, Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. China; Graduate University of the Chinese Academy of Sciences, Beijing 100039, P. R. China.
Macromol Rapid Commun. 2010 Jun 2;31(11):991-7. doi: 10.1002/marc.200900821. Epub 2010 Mar 4.
Synthetic glycopolypeptides have attracted much interest for application in biomedical field as they are structural mimics to the natural glycopeptides or glycoproteins. However, the synthesis methods toward glycopolypeptides are still few or less efficient. Herein, we present a facile route to preparation of glycopolypeptides with highly effective "glycosylation" by click postpolymerization modification. First, an alkyne-substituted N-carboxyanhydride (NCA) monomer was synthesized and subsequently polymerized to afford the polypeptide with "clickable" alkyne pendants. The alkyne-functionalized polypeptide was then "glycosylated" by click reaction of different sugar azides to the alkyne pendants with high efficiency. All the obtained glycopolypeptides were soluble and preferred α-helix conformation in water. Primary studies on the obtained glycopolypeptides binding with Con A lectin were assessed by turbidimetric assay. The more quantitive studies of the interactions between lectin proteins and the synthetic glycopolypeptides, and the application of these materials as the multivalent ligands are in progress.
合成糖多肽作为天然糖肽或糖蛋白的结构模拟物，在生物医学领域的应用引起了广泛关注。然而，合成糖多肽的方法仍然较少或效率较低。在此，我们展示了一种通过点击后聚合修饰制备具有高效“糖基化”的糖多肽的简便途径。首先，合成了一种炔基取代的N-羧基环内酸酐（NCA）单体，随后将其聚合以得到带有“可点击”炔基侧链的多肽。然后，通过不同糖叠氮化物与炔基侧链的高效点击反应，将炔基功能化的多肽进行“糖基化”。所有获得的糖多肽在水中均溶解且具有优先的α-螺旋构象。通过比浊法评估了所获得的糖多肽与伴刀豆球蛋白A凝集素结合的初步研究。关于凝集素蛋白与合成糖多肽之间相互作用的更定量研究以及这些材料作为多价配体的应用正在进行中。
