Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins

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Wawryszyn , M , Sauter , P F , Nieger , M , Koos , M R M , Koehler , C , Luy , B , Lemke , E A & Bräse , S 2018 , ' Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins ' , European Journal of Organic Chemistry , no. 31 , pp. 4296-4305 . https://doi.org/10.1002/ejoc.201800602

Title: Synthesis of Azido-Glycans for Chemical Glycomodification of Proteins
Author: Wawryszyn, Mirella; Sauter, Paul F.; Nieger, Martin; Koos, Martin R. M.; Koehler, Christine; Luy, Burkhard; Lemke, Edward A.; Bräse, Stefan
Contributor: University of Helsinki, Department of Chemistry
Date: 2018-08-23
Language: eng
Number of pages: 10
Belongs to series: European Journal of Organic Chemistry
ISSN: 1434-193X
URI: http://hdl.handle.net/10138/324818
Abstract: Chemically produced, accurately linkable oligosaccharides are of importance for the synthesis of neo-glycoproteins. On the route to high-mannose type N-glycans, we present a convenient synthesis of several glycans bearing an azide moiety at the reducing end. An azido-glycan core structure as valuable precursor was modified into the protected N-glycan pentasaccharide core structure and the possibility of modular attachment of different antenna was demonstrated through synthesis of a pentamannose donor and glycosylation with the core structure. The azido function allows for chemical ligation with recombinantly modified proteins featuring noncanonical cyclooctyne amino acids, providing access to customized glycopatterns of glycoproteins, e.g., of antibodies that are of high interest for biopharmaceutical applications.
Subject: Synthetic methods
N-Glycans
Glycoforms
Glycoproteins
Oligosaccharides
High-Mannose Motif
HIGH-MANNOSE-TYPE
GENETIC-CODE EXPANSION
FC-GAMMA-RIII
N-GLYCANS
CHEMOENZYMATIC SYNTHESIS
COUPLING-CONSTANTS
DESIGNER PROTEINS
CORE FUCOSE
GLYCOSYLATION
EFFICIENT
116 Chemical sciences
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