Highly Efficient Synthesis of Multiantennary Bisected N-glycans Based on Imidates

Manuel Mönnich, Steffen Eller, Theodoros Karagiannis, Lukas Perkams, Thomas Luber, Dimitri Ott, Mathäus Niemietz, Joanna Hoffman, Janika Walcher, Lukas Berger, Matthias Pischl, Markus Weishaupt, Cathrin Wirkner, Rachel G. Lichtenstein, Carlo Unverzagt

Research output: Contribution to journalArticlepeer-review

22 Scopus citations

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 languageEnglish
Pages (from-to)10487-10492
Number of pages6
JournalAngewandte Chemie - International Edition
Volume55
Issue number35
DOIs
StatePublished - 22 Aug 2016

Keywords

  • carbohydrates
  • glycosylation
  • oligosaccharides
  • protecting groups
  • synthetic methods

ASJC Scopus subject areas

  • Catalysis
  • Chemistry (all)

Fingerprint

Dive into the research topics of 'Highly Efficient Synthesis of Multiantennary Bisected N-glycans Based on Imidates'. Together they form a unique fingerprint.

Cite this