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Multivalent glycocyclopeptides: conjugation methods and biological applications
Chemical Society Reviews ( IF 46.2 ) Pub Date : 2022-10-04 , DOI: 10.1039/d2cs00640e
David Goyard 1 , Angela Martin-Serrano Ortiz 1 , Didier Boturyn 1 , Olivier Renaudet 1
Affiliation  

Click chemistry was extensively used to decorate synthetic multivalent scaffolds with glycans to mimic the cell surface glycocalyx and to develop applications in glycosciences. Conjugation methods such as oxime ligation, copper(I)-catalyzed alkyne–azide cycloaddition, thiol–ene coupling, squaramide coupling or Lansbury aspartylation proved particularly suitable to achieve this purpose. This review summarizes the synthetic strategies that can be used either in a stepwise manner or in an orthogonal one-pot approach, to conjugate multiple copies of identical or different glycans to cyclopeptide scaffolds (namely multivalent glycocyclopeptides) having different size, valency, geometry and molecular composition. The second part of this review will describe the potential of these structures to interact with various carbohydrate binding proteins or to stimulate immunity against tumor cells.

中文翻译:

多价糖环肽:偶联方法和生物学应用

点击化学被广泛用于用聚糖装饰合成多价支架以模拟细胞表面糖萼并开发糖科学中的应用。偶联方法如肟连接、铜(I)-催化的炔烃-叠氮化物环加成、硫醇-烯偶联、方酰胺偶联或兰斯伯里天冬氨酰化证明特别适合实现这一目的。本综述总结了可以以逐步方式或正交一锅法使用的合成策略,以将相同或不同聚糖的多个拷贝缀合到具有不同大小、化合价、几何形状和分子的环肽支架(即多价糖环肽)上。作品。本综述的第二部分将描述这些结构与各种碳水化合物结合蛋白相互作用或刺激对肿瘤细胞免疫的潜力。
更新日期:2022-10-04
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