title: Highly Efficient Synthesis of Multiantennary Bisected N-glycans Based on Imidates.
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.
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Manuel
authors.initials: M
authors.lastname: Mönnich
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Steffen
authors.initials: S
authors.lastname: Eller
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Theodoros
authors.initials: T
authors.lastname: Karagiannis
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Lukas
authors.initials: L
authors.lastname: Perkams
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Thomas
authors.initials: T
authors.lastname: Luber
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Dimitri
authors.initials: D
authors.lastname: Ott
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Mathäus
authors.initials: M
authors.lastname: Niemietz
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Joanna
authors.initials: J
authors.lastname: Hoffman
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Janika
authors.initials: J
authors.lastname: Walcher
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Lukas
authors.initials: L
authors.lastname: Berger
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Matthias
authors.initials: M
authors.lastname: Pischl
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Weishaupt
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany.
authors.forename: Cathrin
authors.initials: C
authors.lastname: Wirkner
authors.affiliation: Department of Biotechnology Engineering, Ben-Gurion University of the Negev, Beer-Sheva, 84105, Israel.
authors.forename: Rachel G
authors.initials: RG
authors.lastname: Lichtenstein
authors.affiliation: Bioorganische Chemie, Gebäude NW1, Universität Bayreuth, 95440, Bayreuth, Germany. carlo.unverzagt@uni-bayreuth.de.
authors.forename: Carlo
authors.initials: C
authors.lastname: Unverzagt
keywords: carbohydrates; glycosylation; oligosaccharides; protecting groups; synthetic methods