Title

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

Document Type

Poster

Department

Chemistry

Conference Title

Annual Conference of the Society for Glycobiology

Organization

Society for Glycobiology

Location

San Diego, CA

Conference Dates

December 3-6, 2003

Date of Presentation

12-3-2003

Abstract

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.

This document is currently not available here.

Share

COinS