title: Strategies for the synthesis and screening of glycoconjugates. 1. A library of glycosylamines.
abstract: 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.
authors.affiliation: Affymax Research Institute, Palo Alto, California 94304, USA.
authors.forename: D
authors.initials: D
authors.lastname: Vetter
authors.forename: M A
authors.initials: MA
authors.lastname: Gallop
mesh_terms: D002240:Carbohydrate Sequence; D005944:Glucosamine / Q000737:chemistry*; D006001:Glycoconjugates / Q000032:analysis / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data
chemical_list: D006001:Glycoconjugates; D005944:Glucosamine