Zymetx, Inc.

Ole Hingsgaul

David R Bundle

Om P Srivastava

Minghui Du

Geeta Srivastava

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.

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Edmonton, Canada

Ole Hingsgaul