Abstract
The occurrence of N-glycans with a bisecting GlcNAc modification on glycoproteins has many implications in developmental and immune biology. However, these particular N-glycans are difficult to obtain either from nature or through synthesis. We have developed a flexible and general method for synthesizing bisected N-glycans of the complex type by employing modular TFAc-protected donors for all antennae. The TFAc-protected N-glycans are suitable for the late introduction of a bisecting GlcNAc. This integrated strategy permits for the first time the use of a single approach for multiantennary N-glycans as well as their bisected derivatives via imidates, with unprecedented yields even in a one-pot double glycosylation. With this new method, rare N-glycans of the bisected type can be obtained readily, thereby providing defined tools to decipher the biological roles of bisecting GlcNAc modifications.
Original language | English |
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Pages (from-to) | 10487-10492 |
Number of pages | 6 |
Journal | Angewandte Chemie - International Edition |
Volume | 55 |
Issue number | 35 |
DOIs | |
State | Published - 22 Aug 2016 |
Keywords
- carbohydrates
- glycosylation
- oligosaccharides
- protecting groups
- synthetic methods
ASJC Scopus subject areas
- Catalysis
- General Chemistry