Synthesis and NMR-Analysis of 2-Amino-2-Deoxy-Mannuronic Acid Derivatives
Annual Conference of the Society for Glycobiology
Society for Glycobiology
San Diego, CA
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.
Chiu, T. M.,
Gross, P. H.,
Franz, A. H.
Synthesis and NMR-Analysis of 2-Amino-2-Deoxy-Mannuronic Acid Derivatives.
Paper presented at Annual Conference of the Society for Glycobiology in San Diego, CA.