We found a match
Your institution may have access to this item. Find your institution then sign in to continue.
- Title
One-Pot Synthesis of Unprotected Anomeric Glycosyl Thiols in Water for Glycan Ligation Reactions with Highly Functionalized Sugars.
- Authors
Köhling, Sebastian; Rademann, Jörg; Schiller, Jürgen; Exner, Matthias P.; Nojoumi, Saba; Budisa, Nediljko
- Abstract
Chemical synthesis of oligosaccharide conjugates is essential for studying the functional relevance of carbohydrates, and this task would be facilitated considerably if reliable methods for the anomeric ligation of unprotected sugars in water were available. Here, a method for the preparation of anomeric glycosyl thiols from complex unprotected mono-, di-, and oligosaccharides is presented. By exploiting the neighboring-group effect of the 2-acetamido-group, 1,2-oxazolines are generated and converted into 1-glycosyl thioesters through treatment with 1-thioacids. The unprotected anomeric glycosyl thiolates released in situ were conjugated to Michael acceptors, aliphatic halogenides, and aziridines to furnish versatile glycoconjugates. Conjugation of amino acids and proteins was accomplished using the thiol-ene reaction with terminal olefins. This method gives efficient access to anomeric glycosyl thiols and thiolates, which enables anomeric ligations of complex unprotected glycans in water.
- Subjects
GLYCOSIDES; SACCHARIDES; GLYCANS; LIGATION reactions; OLIGOSACCHARIDE synthesis; THIOESTERS; EUKARYOTIC cells
- Publication
Angewandte Chemie International Edition, 2016, Vol 55, Issue 50, p15510
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201607228