Strategies for the synthesis and screening of glycoconjugates. 1. A library of glycosylamines.
A simple one-step procedure is found to be highly effective for the "functionalization" of glycodiversity. This study encompasses 50 unprotected mono- and oligosaccharides, which are subjected to Kochetkov aminations in saturated aqueous ammonium carbonate. The reaction allows for the stereo- and regioselective introduction of an amino group into all oligosaccharides tested, as well as into a great variety of monosaccharides including charged species. The resulting unprotected glycosylamines are stable compounds, and the inherent amino group provides a convenient site for chemoselective conjugation and modification as described in the following paper in this issue.
Vetter
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Affymax Research Institute, Palo Alto, California 94304, USA.
Gallop
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D002240:Carbohydrate Sequence; D005944:Glucosamine / Q000737:chemistry*; D006001:Glycoconjugates / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data
D006001:Glycoconjugates; D005944:Glucosamine