Other

Glycomed, Inc.

Zymetx, Inc.

Geeta Srivastava

David R Bundle

Om P Srivastava

Minghui Du

Ole Hindsgaul

Kevin R Holme

Roman Szweda

Avraham Liav

H Rizk Hanna

Frank W Barresi

Ole Hingsgaul

The present invention provides improved method of preparing a 4-O-alkyl chromogenic ketoside of N-acetylneuraminic acid (Neu5Ac) and a 7-O-alkyl chromogenic ketoside of N-acetylneuraminic acid (Neu5Ac) for use in the selective detection of various influenza viruses and parainfluenza viruses. The ketosides are substrates that are selectively cleaved by a neuraminidase on the virus to be detected, but not by neuraminidases found on other viruses or on bacteria, or on the cells of the host. The syntheses are efficient and provide large quantities of the ketosides for commercial development. The synthesis includes a step of alkylating the 4- or 7-hydroxyl groups of a protected alkyl ester alkyl ketoside derivative of Neu5Ac by processes that include contacting the derivative with a composition comprising an alkyl halide to form a 4- or a 7-O-alkyl protected alkyl ester alkyl ketoside derivative of Neu5Ac. The syntheses alternatively include protecting the 8- and 9-hydroxyl groups of an alkyl ester alkyl ketoside derivative of Neu5Ac by forming an 8,9-ketal or an 8,9-epoxide protected alkyl ester alkyl ketoside derivative of Neu5Ac.

Syntheses of 4-alkyl chromogenic glycosides and 7-alkyl chromogenic glycosides of N-acetylneuraminic acids

The present invention provides an improved method of preparing a 4,7-di-O-alkyl chromogenic ketoside of N-acetylneuraminic acid (Neu5Ac) for use in detecting influenza virus types A and B. The ketosides are substrates that are selectively cleaved by a neuraminidase on influenza virus, but not be neuraminidases found on other viruses or on bacteria. The synthesis is efficient and provides large quantities of the ketoside for commercial development. The synthesis includes a step of alkylating the 4- and 7-hydroxyl groups of a protected alkyl ester alkyl ketoside derivative of Neu5Ac by a process that comprises contacting the derivative with a composition comprising an alkyl halide to form a 4,7-di-O-alkyl protected alkyl ester alkyl ketoside derivative of Neu5Ac. The synthesis alternatively includes protecting the 8- and 9-hydroxyl groups of an alkyl ester alkyl ketoside derivative of Neu5Ac by forming an 8,9-epoxide protected alkyl ester alkyl ketoside derivative of Neu5Ac.

Synthesis of 4,7-dialkyl chromogenic glycosides of N-acetylneuraminic acids

Disclosed are novel oligosaccharide glycosides having mammalian immunosuppressive and tolerogenic properties, pharmaceutical compositions containing such oligosaccharide glycosides and to methods of using such oligosaccharide glycosides to modulate cell-mediated immune responses in a mammal.

Oligosaccharide glycosides having mammalian immunosuppresive and

Growing community of inventors

Edmonton, Canada

Geeta Srivastava