Oklahoma Medical Research Foundation

Gregory A Turner

Avraham Liav

James F Maher

Michael D Roark

C Worth Clinkscales

Sheri Blystone

Ragen F Hardgrave

Chromogenic derivatives of N-acetylneuraminic acid modified in the 4-position to contain a hydrogen atom, a fluorine atom, a methoxy group, or an ethoxy group are used as substrates in colorimetric assays for human influenza neuraminidase activity in clinical specimens for the purpose of selectively diagnosing influenza infection. The substrates may exhibit different reactivity with the different types of influenza neuraminidases, thus enabling one to discern the specific type of influenza infection and prescribe appropriate treatment and/or supportive therapy therefor.

Methods for diagnosing human influenza and 4-position modified

This invention relates to an improved process for the synthesis of 4-alkoxy-N-acetylneuraminic acids. According to the process of the invention, N-acetylneuraminic acid is first alkylated at C-1 and C-2 and then the vicinal hydroxyl groups at C-8 and C-9 are protected through the formation of a ketal. The resulting protected alkyl ester alkyl ketoside is then alkylated at the C-4 position whereby the hydrogen of the C-4 hydroxyl group is replaced with an alkyl group to form an alkoxy group. Deprotection is accomplished through the removal of the ketal group at C-8 and C-9 and removal of the alkyl groups at C-1 and C-2, thereby producing the 4-alkoxy-N-acetylneuraminic acid.

Synthesis of 4-alkoxy-N-acetylneuraminic acid

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Independence, MO, United States of America

Gregory A Turner