Synthesis of Differentially Protected Glucosamine Building Blocks and Their Evaluation as Glycosylating Agents |
| |
| Authors: | Pascal Bindschädler Lukas O Dialer Peter H Seeberger |
| |
| Institution: | 1. Laboratory for Organic Chemistry , Swiss Federal Institute of Technology (ETH) Zürich , Wolfgang-Pauli-Strasse 10, CH-8093, Zürich, Switzerland;2. Max-Planck-Institute of Colloids and Interfaces, Department of Biomolecular Systems , Am Mühlenberg 1, 14476, Potsdam-Golm, Germany |
| |
| Abstract: | The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for α-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in α-selective couplings to protected l-iduronic acid derivatives. |
| |
| Keywords: | Heparin Oligosaccharides Carbohydrates Glycosylation 4-Nitrobenzenesulphonamide protecting group 2 4-Dinitrophenyl protecting group |
|
|
