Synthesis of Azido‐Glycans for Chemical Glycomodification of Proteins. Issue 31 (9th August 2018)

• Record Type: Journal Article
• Authors: Wawryszyn, Mirella; Sauter, Paul F.; Nieger, Martin; Koos, Martin R. M.; Koehler, Christine; Luy, Burkhard; Lemke, Edward A.; Bräse, Stefan
• Is Part Of: European journal of organic chemistry. Issue 31(2018)
• Page Start: 4296
• Page End: 4305
• Publication Date: 2018-08-09
• Subjects: Synthetic methods -- N‐Glycans -- Glycoforms -- Glycoproteins -- Oligosaccharides -- High‐Mannose Motif; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800602
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : An azido‐glycan core structure was modified into the protected N ‐glycan pentasaccharide 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.