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

Autor: Mönnich, Manuel, Eller, Steffen, Karagiannis, Theodoros, Perkams, Lukas, Luber, Thomas, Ott, Dimitri, Niemietz, Mathäus, Hoffman, Joanna, Walcher, Janika, Berger, Lukas, Pischl, Matthias, Weishaupt, Markus, Wirkner, Cathrin, Lichtenstein, Rachel G., Unverzagt, Carlo
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Zdroj: Angewandte Chemie International Edition; 8/22/2016, Vol. 55 Issue 35, p10487-10492, 6p
Abstrakt: 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. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index