title: Synthesis of multiantennary complex type N-glycans by use of modular building blocks.
abstract: A modular set of oligosaccharide building blocks was developed for the synthesis of multiantennary N-glycans of the complex type, which are commonly found on glycoproteins. The donor building blocks were laid out for the elongation of a core trisaccharide acceptor (beta-mannosyl chitobiose) conveniently protected with a single benzylidene moiety at the beta-mannoside. Through two consecutive regio- and stereoselective couplings the donors gave N-glycans with three to five antennae in high yields. Due to the consistent protection group pattern of the donors the deprotection of the final products can be performed by using a general reaction sequence.
authors.affiliation: Bioorganische Chemie, Universität Bayreuth, Gebäude NW1, 95440 Bayreuth, Germany. carlo.unverzagt@uni-bayreuth.de
authors.forename: Carlo
authors.initials: C
authors.lastname: Unverzagt
authors.forename: Gislinde
authors.initials: G
authors.lastname: Gundel
authors.forename: Steffen
authors.initials: S
authors.lastname: Eller
authors.forename: Ralf
authors.initials: R
authors.lastname: Schuberth
authors.forename: Joachim
authors.initials: J
authors.lastname: Seifert
authors.forename: Harald
authors.initials: H
authors.lastname: Weiss
authors.forename: Mathäus
authors.initials: M
authors.lastname: Niemietz
authors.forename: Matthias
authors.initials: M
authors.lastname: Pischl
authors.forename: Claudia
authors.initials: C
authors.lastname: Raps
mesh_terms: D002236:Carbohydrate Conformation; D004187:Disaccharides / Q000138:chemical synthesis / Q000737:chemistry; D006023:Glycoproteins / Q000138:chemical synthesis / Q000737:chemistry; D008362:Mannosides / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry; D011134:Polysaccharides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D004187:Disaccharides; D006023:Glycoproteins; D008362:Mannosides; D009844:Oligosaccharides; D011134:Polysaccharides; C032438:chitobiose