posted on 2022-02-11, 22:00authored byYuankun Dao, Weidong Dong, Jun Zhang, Suwei Dong
N-glycans in eukaryotic proteins are commonly attached to asparagine residues via β-N-glycosidic linkages, which are susceptible to glycosidases, such as PNGase. Here we report the preparation of α-N-glycosylated peptides based on the solid-phase peptide synthesis strategy using an α-N-GlcNAc-containing asparagine building block, and a transglycosylation reaction of oligosaccharide oxazoline promoted by endoglycosidases CCN180H. The resultant glycopeptide, bearing the complex-type α-N-sialyl undecasaccharide, exhibits resistance against PNGase F, which may be of potential use in studying the catabolism of N-glycans and glycoengineering those peptide-based therapeutics.
Funding
The authors are grateful for financial support from the Beijing Natural Science Foundation (No. JQ18024), the National Natural Science Foundation of China (Nos. 21822701, 91953111, and 21672012), and the Beijing Outstanding Young Scientist Program (No. BJJWZYJH01201910001001).