Leiden Institute of Chemistry, Leiden University, Einsteinweg 55, 2333 CC Leiden, The Netherlands.
Org Biomol Chem. 2022 Aug 24;20(33):6487-6507. doi: 10.1039/d2ob00829g.
Protein glycosylation is a key post-translational modification important to many facets of biology. Glycosylation can have critical effects on protein conformation, uptake and intracellular routing. In immunology, glycosylation of antigens has been shown to play a role in self/non-self distinction and the effective uptake of antigens. Improperly glycosylated proteins and peptide fragments, for instance those produced by cancerous cells, are also prime candidates for vaccine design. To study these processes, access to peptides bearing well-defined glycans is of critical importance. In this review, the key approaches towards synthetic, well-defined glycopeptides, are described, with a focus on peptides useful for and used in immunological studies. Special attention is given to the glycoconjugation approaches that have been developed in recent years, as these enable rapid synthesis of various (unnatural) glycopeptides, enabling powerful carbohydrate structure/activity studies. These techniques, combined with more traditional total synthesis and chemoenzymatic methods for the production of glycopeptides, should help unravel some of the complexities of glycobiology in the near future.
蛋白质糖基化是一种重要的翻译后修饰，对生物学的许多方面都很重要。糖基化可以对蛋白质构象、摄取和细胞内路由产生关键影响。在免疫学中，抗原的糖基化已被证明在自我/非自我区分和抗原的有效摄取中发挥作用。未糖基化的蛋白质和肽片段，例如癌细胞产生的蛋白质和肽片段，也是疫苗设计的主要候选物。为了研究这些过程，获得具有明确糖基的肽是至关重要的。在这篇综述中，描述了合成具有明确定义的糖肽的关键方法，重点介绍了在免疫学研究中有用和使用的肽。特别关注近年来开发的糖基化方法，因为这些方法能够快速合成各种（非天然）糖肽，从而能够进行强大的碳水化合物结构/活性研究。这些技术，结合传统的全合成和化学酶法生产糖肽，应该有助于在不久的将来揭示糖生物学的一些复杂性。
