Synthesis and NMR-Analysis of 2-Amino-2-Deoxy-Mannuronic Acid Derivatives

Document Type




Conference Title

Annual Conference of the Society for Glycobiology


Society for Glycobiology


San Diego, CA

Conference Dates

December 3-6, 2003

Date of Presentation



Aminosugars constitute abundant building blocks of naturally occurring polysaccharides or antibiotics. The most frequently found aminosugars are members of the class of 2-amino-2-D-hexoses. N-Acetyl-D-glucosamine for example is a major constituent of biologically important polysaccharides such as hyaluronic acid, dermatan sulfate, keratan sulfate, and is the anchor for N-linked glycans in many glycoproteins. N-Acetyl-D-galactosamine can be found in the chondroitin sulfate family and as the O-glycosidically linked unit in many glycosylated proteins. It has been shown that metabolic pathways of N-acetyl-D-glucosamine and N-acetyl-D-mannosamine can be exploited for cell surface engineering. Altered cell surface oligosaccharides offer thus a way for the study of cell-cell interactions. For such studies to be meaningful, it is important to have well-characterized simple carbohydrate building blocks and synthetic strategies in hand. This paper reports the synthesis of 2-amino-2-deoxy derivatives of D-altrose, D-allose, D-glucose, and D-mannose starting from D-glucose. The protected mannosamines were subsequently converted into 2-amino-2-deoxy-mannuronic acids by oxidation. The structures of the products were confirmed by 1H-, 13C-, 1H-1H-COSY, and 1H-13C-COSY (HETCOR) Nuclear Magnetic Resonance (NMR) spectroscopy. Observed coupling constants were correlated with the molecule’s average solution conformation by the Karplus equation.

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